Citric Acid → Ethyl 2-benzyl-3-oxopropanoate
Reaction equation
[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]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- additionwere added dropwise under ice
- temperaturecool for one hour
- additioneach part was added separately
- stirringAfterwards, the solution mixture was stirred at room temperature for 15 hours
- customreaction solution
- extractionthe reaction solution was extracted with ethyl acetate
- concentrationthe extract was concentrated under reduced pressure
- customto obtain 32.4 g of a brown oily concentrate
- concentrationThe concentrate thus
- customobtained
- customwas purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-072297d6388b42499252a23ee3c7cb95
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07666659B2
Reaction notes
Loading…