Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoate → 3-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester

HRID 432074Notes

Reaction equation

HRID 432074 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:21][CH2:22][CH3:23])=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH3:2]>CO.[Rh]>[CH2:1]([O:3][C:4](=[O:24])[CH:5]([O:21][CH2:22][CH3:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 54423854Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoate

Product 1

HCID 110779683-(4-Benzyloxyphenyl)-2-ethoxypropanoic acid ethyl esterYield 10,150,156%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

3-(4-Benzyloxyphenyl)-2-ethoxyacrylic acid ethyl ester (0.5 g; 1.5 nmole) was hydrogenated at atmospheric pressure using rhodium on charcoal as catalyst (5%, 50 mg) in methanol (20 ml). The crude product was purified by chromatography using heptane:ethyl acetate (5:1) as eluant to give 50 mg (yield 10%) of 3-(4-benzyloxyphenyl)-2-ethoxypropanoic acid ethyl ester.

Workup

  1. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-dd17ab42970c4ecbada3307ffdc58033
Source dataset
uspto-grants-2003_12
Patent number
US06660879B2

Reaction notes

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