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Jin, Yinghua; Roberts, Frank G.; Coates, Robert M. (2007). "Stereoselective
Isoprenoid Chain Extension with Acetoacetate Dianion: [(
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stabilized. The carbon then undergoes nucleophilic substitution. When heated with aqueous acid, the newly alkylated ester is
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is alkylated at the α-carbon to both carbonyl groups and then converted into a ketone, or more specifically an α-substituted
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A strong base deprotonates the dicarbonyl α-carbon. This carbon is preferred over the methyl carbon because the formed
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The classical acetoacetatic ester synthesis utilizes the 1:1 conjugate base. Ethyl acetoacetate is however diprotic:
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to form a methyl ketone. The alkylated ester can undergo a second substitution to produce the dialkylated product.
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Et) adds electrophile to the terminal carbon as depicted in the following simplified form:
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Acetoacetic Ester
Synthesis – Alkylation of Enolates | PharmaXChange.info
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218:Double deprotonation of ethyl acetoacetate
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409:Carbon-carbon bond forming reactions
174:Acetoacetic ester synthesis equation
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155:is a chemical reaction where
331:Organic Chemistry: Second Ed
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21:Acetoacetic ester synthesis
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203:to a β-keto acid, which is
153:Acetoacetic ester synthesis
125:acetoacetic-ester-synthesis
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163:. This is very similar to
329:Smith, Janice Gorzynski.
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120:Organic Chemistry Portal
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379:10.15227/orgsyn.084.0043
361:)-Geranylgeraniol from (
311:Malonic ester synthesis
272:The dianion (i.e., LiCH
165:malonic ester synthesis
47:Acetoacetic acid esters
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90:α-substituted acetone
260:Et + BuLi → LiCH
399:Coupling reactions
333:. 2008. pp 905–906
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157:ethyl acetoacetate
404:Organic reactions
367:Organic Syntheses
292:Et + RX → RCH
238:Et + NaH → CH
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30:Coupling reaction
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296:C(O)CH(Na)CO
288:C(O)CH(Na)CO
276:C(O)CH(Na)CO
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264:C(O)CH(Na)CO
256:C(O)CH(Na)CO
242:C(O)CH(Na)CO
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152:
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140:RXNO:0000107
135:ontology ID
115:Identifiers
105:Temperature
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100:Conditions
69:O-R & H
393:Categories
317:References
300:Et + LiX
268:Et + BuH
201:hydrolyzed
193:conjugated
197:resonance
195:and thus
183:Mechanism
36:Reaction
305:See also
246:Et + H
359:E, E, E
189:enolate
161:acetone
373:: 43.
230:C(O)CH
363:E, E
284:LiCH
375:doi
191:is
133:RSC
58:R-X
395::
371:84
369:.
349:^
252:CH
234:CO
226:CH
167:.
109:+Δ
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298:2
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258:2
254:3
248:2
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240:3
236:2
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228:3
82:↓
73:O
71:3
67:(
65:+
54:+
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