Citric Acid → Ethyl 2-benzyl-3-oxopropanoate

HRID 1445305

反応式

HRID 1445305 の反応式
[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]

参加物

6

反応物 4

HCID 311Citric AcidHCID 8025Ethyl formate2 回HCID 16237Ethyl 3-phenylpropionateHCID 24758Sodium hydride2 回

生成物 1

HCID 562571Ethyl 2-benzyl-3-oxopropanoate収率 86.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-072297d6388b42499252a23ee3c7cb95
出典データセット
uspto-grants-2010_02
特許番号
US07666659B2

関連ノート

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