Ethyl Acetate → Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

HRID 987275Notes

Reaction equation

HRID 987275 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C@H:16]([O:20][CH2:21][CH3:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:23](OCC)(=O)[CH3:24]>[Pd]>[CH2:23]([O:19][C:17](=[O:18])[C@@H:16]([O:20][CH2:21][CH3:22])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=1)[CH3:24]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 11044786(S)-3-(4-(Benzyloxy)phenyl)-2-ethoxypropanoic acid

Product 1

HCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoateYield 76%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-(4-Benzyloxyphenyl)-2-(S)-ethoxypropanoic acid (7.13 g; 21.7 mmole) was hydrogenated at atmospheric pressure for 2 hours in ethyl acetate (70 ml) using Pd/C as catalyst. Purification by chromatography on silica gel using toluene:ethyl acetate as eluant gave 3.83 g (yield in 3 step 76%) of (S)-2-ethoxy-3-(4-hydroxyphenyl)propanoic acid ethyl ester.

Workup

  1. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-caf95dd5ee3346559c3d50f01f669c98
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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