Ethyl benzoylformate → (-)-Ethyl mandelate

HRID 2166214Notes

Reaction equation

HRID 2166214 reaction equation
[C:1]1([C:7](=[O:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CN(C=O)C>[OH:13][C@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

3

Reactant 1

HCID 15349Ethyl benzoylformate

Product 1

HCID 6951556(-)-Ethyl mandelateYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl phenylglyoxylate (1.6 mmol) was asymmetrically reduced in the same manner as in Example 6, except that DMF was used as the reaction medium, giving 0.25 g of ethyl (R)-(-)-2-hydroxy-2-phenylacetate, having specific rotation [α]D20 of 38.8° (cl. 00, CHCl3). The synthesis yield was 80% and the optical yield was 75% e.e.

Sources & evidence

ORD record
ord-4f906e0072054aeb9eb46d916e186a87
Source dataset
uspto-grants-1990_07
Patent number
US04943652

Reaction notes

Loading…