Citric Acid → Ethyl 2-benzyl-3-oxopropanoate

HRID 1445305

반응식

HRID 1445305 반응식
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:16](OCC)=[O:17].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH:16]([CH:10]([CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 8025Ethyl formate2회HCID 16237Ethyl 3-phenylpropionateHCID 24758Sodium hydride2회

생성물 1

HCID 562571Ethyl 2-benzyl-3-oxopropanoate수율 86.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension solution containing 4.4 g of 60% NaH in 200 ml of THF, 17.8 g of ethyl 3-phenylpropionate and 8.2 g of ethyl formate were added dropwise under ice cool for one hour. Thereafter, the mixture was stirred at room temperature for 15 hours. Furthermore, 14 g of 60 % NaH and 25.9 g of ethyl formate were divided into three parts and each part was added separately. Afterwards, the solution mixture was stirred at room temperature for 15 hours. After a 10% citric acid solution was added to the resultant reaction solution, the reaction solution was extracted with ethyl acetate and the extract was concentrated under reduced pressure to obtain 32.4 g of a brown oily concentrate. The concentrate thus obtained was purified by silica gel column chromatography to obtain 17.9 g of the titled compound as a transparent oily substance.

후처리

  1. additionwere added dropwise under ice
  2. temperaturecool for one hour
  3. additioneach part was added separately
  4. stirringAfterwards, the solution mixture was stirred at room temperature for 15 hours
  5. customreaction solution
  6. extractionthe reaction solution was extracted with ethyl acetate
  7. concentrationthe extract was concentrated under reduced pressure
  8. customto obtain 32.4 g of a brown oily concentrate
  9. concentrationThe concentrate thus
  10. customobtained
  11. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-072297d6388b42499252a23ee3c7cb95
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666659B2

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