Aluminium lithium hydride → 3-(4-Bromo-2-trifluoromethoxy-phenyl)-propan-1-ol

HRID 1984905Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[O:20][C:21]([F:24])([F:23])[F:22])C>CCOCC>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH2:11][CH2:10][OH:9])=[C:14]([O:20][C:21]([F:22])([F:23])[F:24])[CH:15]=1

Participants

Conditions

Temperature: 4 °C

Procedure

A suspension of lithium aluminum hydride (834 mg, 22.0 mmol) in Et2O (20 mL) was cooled at 4° C. A solution of (E)-3-(4-bromo-2-trifluoromethoxy-phenyl)-acrylic acid ethyl ester (2.98 g, 8.79 mmol) in Et2O (9 mL) was added dropwise, and the mixture was stirred at ambient temperature for 90 min. The reaction was quenched with EtOAc (6 mL) and saturated aqueous NH4Cl was added dropwise. The aqueous layer was extracted with EtOAc (three times). The combined organic layer was washed with 1 M aqueous HCl, dried over MgSO4, filtered, concentrated, and purified by flash chromatography (silica gel, 25% EtOAc in hexane) to give 3-(4-bromo-2-trifluoromethoxy-phenyl)-propan-1-ol (1.14 g, 43%) as a colorless oil.

Workup

customThe reaction was quenched with EtOAc (6 mL) and saturated aqueous NH4Cl
additionwas added dropwise
extractionThe aqueous layer was extracted with EtOAc (three times)
washThe combined organic layer was washed with 1 M aqueous HCl
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by flash chromatography (silica gel, 25% EtOAc in hexane)

Sources & evidence

ORD record: ord-9301b75703e64ea984f3de233a419ac7
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544690B2

Reaction notes

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