Ethyl alpha-oxobenzenebutanoate → Ethyl 2-hydroxy-4-phenylbutyrate, (+-)-

HRID 651350

Reaction equation

HRID 651350 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[O:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].[H][H]>C1(C)C=CC=CC=1.CO>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([OH:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 562087Ethyl alpha-oxobenzenebutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 4092621Ethyl 2-hydroxy-4-phenylbutyrate, (+-)-

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

The general procedure described in Example B1 is repeated, with the following modifications to the reaction conditions: ethyl-4-phenyl-2-oxobutyrate (substrate): 0.352 g (1.7 mmol); solvent: 10 ml of toluene/methanol (1:1); hydrogen: 50 bar, temperature: 50° C.; reaction time: 19 hours. The conversion is 100%, ee: 44% (R).

Workup

  1. customis repeated, with the following modifications to the reaction conditions
  2. custom50° C.
  3. customreaction time
  4. custom19 hours

Sources & evidence

ORD record
ord-2a15d83e4c9a44eea74e25d3e9238d39
Source dataset
uspto-grants-2001_08
Patent number
USRE037344E1

Linked notes

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