Water → HCID 67146538, compound

HRID 984945Notes

Reaction equation

HRID 984945 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 20768012(E)-3-(4-bromo-phenyl)-3-phenyl-acrylic acid ethyl ester

Product 1

HCID 67146538HCID 67146538, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1.2 M solution of DIBAL-H in toluene (45 ml, 42 mmol) was added dropwise, at −15° C. over 20 min, to a stirred solution of (E)-3-(4-bromophenyl)-3-phenylacrylicacid ethyl ester (6.0 g, 18.1 mmol) in dry THF (80 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 5.2 g of (E)-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-4f4491d9f741495f996cdea06305ac73
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

Loading…