Methyl 3-[4-(benzyloxy)phenyl]propanoate → 3-(4-Benzyloxy-phenyl)-2-ethoxy-propionic acid methyl ester

HRID 1353204Notes

Reaction equation

HRID 1353204 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)C.COC(=O)C(OC)CC1C=CC=C(OCC2C=CC=CC=2)C=1.COC(=O)CCC1C=CC(OCC2C=CC=CC=2)=CC=1>>[CH3:1][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:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoateHCID 54423854Ethyl 3-[4-(benzyloxy)phenyl]-2-ethoxyprop-2-enoateHCID 588226203-(3-Benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester

Product 1

HCID 219309623-(4-Benzyloxy-phenyl)-2-ethoxy-propionic acid methyl esterYield 47.1%

Procedure

The title compound was prepared from 3-(4-Benzyloxy-phenyl)-2-ethoxy-acrylic acid ethyl ester (Preparation 2, step 2) (3.3 gr, 10.12 mmol) via the same procedure used for the preparation of 3-(3-Benzyloxy-phenyl)-2-methoxy-propionic acid methyl ester (example 9, step 3) to produce an oil that was purified by chromatography (silica gel, hexanes/ethyl acetate 6:1) to produce two compounds: 3-(4-Benzyloxy-phenyl)-propionic acid methyl ester (1.5 gr, Rf aprox. 0.65) and the desired compound (1.5 gr, Rf aprox. 0.2). MS (ES) for C19H22O4 [M+NH4]+: 332.3.

Workup

  1. customto produce an oil that
  2. customwas purified by chromatography (silica gel, hexanes/ethyl acetate 6:1)
  3. customto produce two compounds

Sources & evidence

ORD record
ord-fdd63e86c75e49bb8dabf56af0ad6919
Source dataset
uspto-grants-2007_05
Patent number
US07220880B2

Reaction notes

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