Ethyl benzoylformate → (-)-Ethyl mandelate
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
Product 1
Reagents, catalysts & solvents 1
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
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