4-Aminophenethyl alcohol → 2-Chloro-3-[4-(2-hydroxy-ethyl)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester

HRID 709448Notes

Reaction equation

HRID 709448 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[Cl:11][C:12]([Cl:20])([Cl:19])[CH2:13][O:14][C:15](=[O:18])[CH:16]=[CH2:17].COC(=O)C([Cl:34])CC1C=CC(CO)=CC=1>>[Cl:11][C:12]([Cl:20])([Cl:19])[CH2:13][O:14][C:15](=[O:18])[CH:16]([Cl:34])[CH2:17][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 669044-Aminophenethyl alcoholHCID 1817502,2,2-Trichloroethyl acrylateHCID 866502982-Chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester

Product 1

HCID 866502992-Chloro-3-[4-(2-hydroxy-ethyl)-phenyl]-propionic acid 2,2,2-trichloro-ethyl ester

Procedure

The title compound was prepared from 2-(4-amino phenyl)ethanol (6.68 g, 48.7 mmol) and commercially available acrylic acid 2,2,2-trichloroethylester (19.82 g, 97.44 mmol) in the same manner as described for 2-chloro-3-(4-hydroxymethyl-phenyl)-propionic acid methyl ester. The crude product was purified by repeated flash chromatography using DCM/MeOH 95:5 as the eluent and the product was obtained as an oil (1.87 g, 10.7%). 1H NMR (300 MHz, CDCl3): δ 7.15-7.29 (m, 4H), 4.54-4.59 (t, 1H), 3.82-3.85 (m, 3H), 3.38-3.45 (dd, 1H), 3.18-3.25 (dd, 1H), 2.79-2.87 (m, 3H).

Workup

  1. customThe crude product was purified by repeated flash chromatography

Sources & evidence

ORD record
ord-7210f141f7a94eb3a779b8cd260d30a3
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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