Water → (Z)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-ol

HRID 984948Notes

Reaction equation

HRID 984948 reaction equation
CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20](=O)/[CH:21]=[C:22](\[C:29]1[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][CH:30]=1)/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)C.O>C1COCC1>[Br:35][C:32]1[CH:31]=[CH:30][C:29](/[C:22](/[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:21]\[CH2:20][OH:19])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 11067512(Z)-3-(4-bromo-phenyl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 22270289(Z)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-olYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.2 M solution of DIBAL-H in toluene (84 ml, 100 mmol) was added dropwise, at −15° C. over 20 min, to a stirred solution of (Z)-3-(4-bromophenyl)-3-phenylacrylicacid ethyl ester (11.1 g, 33.5 mmol) in dry THF (150 ml), and the mixture stirred for 30 min. Rochelles salt and water was carefully added, and the resulting mixture extracted with ethyl acetate (x2). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give 9.3 g of (Z)-3-(4-bromo-phenyl)-3-phenyl-prop-2-en-1-ol.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate (x2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-e60552c2877a4f90af68a9ba47e00d24
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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