Methyl Cinnamate → Methyl 3-phenylpropionate

HRID 1014768Notes

Reaction equation

HRID 1014768 reaction equation
[C:1]([O:11][CH3:12])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)Cl>[C:4]1([CH2:3][CH2:2][C:1]([O:11][CH3:12])=[O:10])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 637520Methyl Cinnamate

Product 1

HCID 7643Methyl 3-phenylpropionateYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of methyl trans cinnamate (49 mg, 0.30 mmol) and rac-32 (9.8 mg, 0.0062 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 48 h. Filtration of the reaction mixture and evaporation of the solvent gave 40 as a clear oil (48 mg, 95%). 1H NMR26 (300 MHz, CDCl3): δ 7.33-7.19 (m, 5H), 3.68 (s, 3H), 2.97 (t, 2H, J=8.1 Hz), 2.65 (t, 2H, J=7.8 Hz); 13C NMR (75.5 MHz, CDCl3): δ 173.4, 140.6, 128.6, 128.4, 126.4, 51.7, 35.8, 31.0.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent

Sources & evidence

ORD record
ord-c77bfcfcbb8141c4a534a21028aba385
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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