406:
373:
31:
333:
420:
437:
467:
ctan-1-yl) which is formed by the action of (3-methyloxetan-3-yl)methanol on activated carboxylic acids in the presence of Lewis acids. The group is base stable and can be cleaved in two steps under mild conditions, mildly acidic hydrolysis yields the ester of tris(hydroxymethyl)ethane which is then
712:
Johnson, William Summer.; Werthemann, Lucius.; Bartlett, William R.; Brocksom, Timothy J.; Li, Tsung-Tee.; Faulkner, D. John.; Petersen, Michael R. (February 1970). "Simple stereoselective version of the
Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene".
635:
Houben, J. "Über die
Condensation von Mercaptanen mit Ameisensäure zu Orthotrithio-ameisensäureestern" [On the condensation of mercaptans with formic acid unto formic acid trithio ortho esters].
491:
483:
405:
385:
345:
332:
372:
749:
687:
195:
Although a less common method, ortho esters were first produced by reaction of 1,1,1-trichloroalkanes with sodium alkoxide:
563:
795:
17:
232:
702:
United States Patent
Application 20070049501, Saini; Rajesh K.; and Savery; Karen, March 1, 2007
227:
Compounds with an adjacent hydrogen atom on R tend to undergo elimination instead. Traditional
133:
Upon standing in the presence of excess alcohol, this intermediate converts to the ortho ester:
764:
Hyo Won Lee and
Yoshito Kishi (1985): "Synthesis of mono- and unsymmetrical bis-orthoesters of
448:
304:
117:
in the presence of one equivalent of hydrogen chloride. The reaction proceeds by formation of
357:
235:. The resulting halogenated compounds undergo ether synthesis like the trichloroalkanes.
800:
452:
397:
612:
DeWolfe, Robert H. (March 1974). "Synthesis of carboxylic or carbonic ortho esters".
8:
243:
114:
75:
745:
683:
587:
559:
39:
773:
722:
667:
653:
645:
617:
551:
472:
389:
47:
30:
476:
106:
250:. Traditional transesterification from a cheaper ortho ester is also possible.
555:
516:
316:
164:
Acid chlorides can also drive the reaction from the corresponding amide, e.g.:
161:
The reaction requires anhydrous conditions, and ideally a nonpolar solvent.
789:
675:
671:
649:
247:
118:
423:
353:
74:
and it is from these that the name 'ortho ester' is derived. An example is
51:
455:. Another example is the bicyclic OBO protecting group (4-methyl-2,6,7-tri
621:
324:
238:
Carboxylic acids naturally form a trithio ortho ester when heated with a
777:
726:
323:; and may be further hydrolyzed (under alkaline conditions) to salts of
487:
427:
264:
71:
67:
239:
393:
320:
711:
586:. Organic Chemistry. Vol. 14. New York, NY: Academic Press.
110:
591:
242:
of appropriate stoichiometry. The resulting compound undergoes
503:
419:
364:
349:
268:
228:
550:. PATAI'S Chemistry of Functional Groups. pp. 623–667.
436:
666:
54:
attached to one carbon atom, i.e. with the general formula
546:
E. H. Cordes (1969). "Ortho Esters". In Saul Patai (ed.).
482:(scyllitol) yields the triply-bridged orthoformate esters
66:. Orthoesters may be considered as products of exhaustive
379:
352:
alcohol with an ortho ester containing a deprotonatable
682:(1st ed.). Oxford University Press. p. 345.
430:, is one of several naturally occurring ortho esters.
231:
can be converted to α,α‑dichloro ethers with
468:cleaved using e.g. an aqueous carbonate solution.
97:, more correctly known as 1,1,1-triethoxyethane.
787:
339:
56:RC(OR<span class="nowrap" style="paddingleft:
315:may be hydrolyzed (under acidic conditions) to
246:to a traditional orthoester in the presence of
638:Berichte der Deutschen Chemischen Gesellschaft
447:Examples of orthoesters include the reagents
545:
577:
575:
494:with two fused adamantane-like skeletons.
27:Chemical group with the structure RC(OR')3
739:
443:: 4-methyl-2,6,7-trioxa-bicyclooctan-1-yl
715:Journal of the American Chemical Society
607:
605:
603:
601:
572:
435:
418:
29:
772:, volume 50, issue 22, pages 4402–4404
758:
611:
581:
541:
539:
537:
14:
788:
386:Bodroux–Chichibabin aldehyde synthesis
380:Bodroux–Chichibabin aldehyde synthesis
598:
534:
105:Ortho esters can be prepared by the
34:The general formula of orthoesters.
24:
744:(3. ed.). Stuttgart: Thieme.
634:
25:
812:
584:Carboxylic Ortho Acid Derivatives
582:DeWolfe, Robert H. (1970).
404:
371:
331:
733:
705:
696:
660:
628:
471:The threefold symmetry of the
13:
1:
740:Kocieński, Philip J. (2005).
527:
388:an ortho ester reacts with a
346:Johnson–Claisen rearrangement
340:Johnson–Claisen rearrangement
267:in mild aqueous acid to form
258:
172: + BzCl → HC(OBz)NH
770:Journal of Organic Chemistry
253:
100:
7:
548:Carboxylic Acids and Esters
497:
412:
183:Cl + ROH → HC(OR)
10:
817:
556:10.1002/9780470771099.ch13
492:scyllitol bis-orthoformate
396:; this is an example of a
263:Ortho esters are readily
119:imido ester hydrochloride
650:10.1002/cber.19120450319
233:phosphorus pentachloride
484:scyllitol orthoformate
449:trimethyl orthoformate
444:
431:
348:is the reaction of an
305:trimethyl orthoformate
35:
439:
422:
358:triethyl orthoacetate
72:orthocarboxylic acids
33:
622:10.1055/s-1974-23268
490:-like skeleton, and
453:triethylorthoacetate
398:formylation reaction
778:10.1021/jo00222a046
727:10.1021/ja00706a074
244:transesterification
445:
432:
76:ethyl orthoacetate
36:
796:Functional groups
751:978-3-13-135603-1
742:Protecting groups
689:978-0-19-850346-0
680:Organic Chemistry
670:; Greeves, Nick;
668:Clayden, Jonathan
50:containing three
40:organic chemistry
16:(Redirected from
808:
780:
762:
756:
755:
737:
731:
730:
709:
703:
700:
694:
693:
664:
658:
657:
654:Internet Archive
652:– via the
632:
626:
625:
609:
596:
595:
579:
570:
569:
543:
473:cyclohexanehexol
408:
390:Grignard reagent
375:
363:
335:
298:
294:
278:
222:
214:
210:
206:
148:
144:
140:
128:
96:
61:
48:functional group
21:
816:
815:
811:
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599:
580:
573:
566:
544:
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415:
382:
362:γ,δ-unsaturated
361:
342:
314:
310:
296:
292:
290:
286:
282:
276:
261:
256:
220:
218:
212:
208:
204:
202:
191:Cl + BzOH.
190:
186:
182:
175:
171:
156:
152:
146:
142:
138:
126:
107:Pinner reaction
103:
95:
91:
87:
83:
79:
65:
59:
55:
28:
23:
22:
15:
12:
11:
5:
814:
804:
803:
798:
782:
781:
757:
750:
732:
721:(3): 741–743.
704:
695:
688:
676:Wothers, Peter
672:Warren, Stuart
659:
627:
616:(3): 153–172.
597:
571:
564:
532:
531:
529:
526:
525:
524:
520:
517:Orthocarbonate
514:
511:
507:
499:
496:
434:
433:
414:
411:
410:
409:
381:
378:
377:
376:
341:
338:
337:
336:
327:and methanol.
317:methyl formate
312:
308:
301:
300:
288:
284:
280:
260:
257:
255:
252:
225:
224:
216:
200:
193:
192:
188:
184:
180:
177:
173:
169:
159:
158:
154:
150:
131:
130:
129:OH + HCl → Cl
102:
99:
93:
89:
85:
81:
63:
57:
26:
9:
6:
4:
3:
2:
813:
802:
799:
797:
794:
793:
791:
779:
775:
771:
767:
761:
753:
747:
743:
736:
728:
724:
720:
716:
708:
699:
691:
685:
681:
677:
673:
669:
663:
655:
651:
647:
644:: 2942–2946.
643:
640:(in German).
639:
631:
623:
619:
615:
608:
606:
604:
602:
593:
589:
585:
578:
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567:
565:9780470771099
561:
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359:
355:
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329:
328:
326:
322:
318:
306:
303:For example,
274:
273:
272:
270:
266:
251:
249:
248:zinc chloride
245:
241:
236:
234:
230:
198:
197:
196:
178:
167:
166:
165:
162:
136:
135:
134:
124:
123:
122:
120:
116:
112:
108:
98:
77:
73:
69:
53:
52:alkoxy groups
49:
45:
41:
32:
19:
769:
768:-inositol".
765:
760:
741:
735:
718:
714:
707:
698:
679:
662:
641:
637:
630:
613:
583:
547:
477:
470:
464:
460:
456:
446:
440:
424:Hygromycin B
383:
360:) to give a
354:alpha carbon
343:
302:
262:
237:
226:
194:
163:
160:
132:
104:
70:of unstable
43:
37:
801:Orthoesters
392:to form an
325:formic acid
113:react with
109:, in which
44:ortho ester
790:Categories
528:References
488:adamantane
428:antibiotic
265:hydrolyzed
259:Hydrolysis
187: + NH
145:OH → RC(OR
68:alkylation
18:Orthoester
614:Synthesis
480:-inositol
254:Reactions
240:mercaptan
179:HC(OBz)NH
101:Synthesis
60:em;">′
678:(2001).
592:70-84226
498:See also
486:with an
413:Examples
394:aldehyde
321:methanol
115:alcohols
111:nitriles
519:, C(OR)
506:, C(OR)
475:isomer
384:In the
350:allylic
287:O → RCO
211:→ RC(OR
137:Cl + 2
125:RCN + R
766:scyllo
748:
686:
590:
562:
504:Acetal
478:scyllo
463:icyclo
356:(e.g.
307:CH(OCH
269:esters
229:esters
221:
205:
139:
426:, an
365:ester
295:+ 2 R
275:RC(OR
168:HCONH
84:C(OCH
46:is a
42:, an
746:ISBN
684:ISBN
588:LCCN
560:ISBN
451:and
344:The
319:and
223:NaCl
207:NaOR
203:+ 3
199:RCCl
153:+ NH
58:0.05
774:doi
723:doi
646:doi
618:doi
552:doi
459:xa-
441:OBO
283:+ H
219:+ 3
38:In
792::
719:92
717:.
674:;
642:45
600:^
574:^
558:.
536:^
400:.
367:.
299:OH
271::
176:Cl
157:Cl
121::
88:CH
80:CH
78:,
776::
754:.
729:.
725::
692:.
656:.
648::
624:.
620::
594:.
568:.
554::
523:.
521:4
512:2
510:R
508:2
465:o
461:b
457:o
313:3
311:)
309:3
297:′
293:′
291:R
289:2
285:2
281:3
279:)
277:′
217:3
215:)
213:′
209:′
201:3
189:4
185:3
181:2
174:2
170:2
155:4
151:3
149:)
147:′
143:′
141:R
127:′
94:3
92:)
90:3
86:2
82:3
64:3
62:)
20:)
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