tert-Butanol → (S)-1-(4-benzyloxyphenyl)-2-bromoethanol

HRID 362939Notes

Reaction equation

[BH4-].[Li+].C(O)(C)(C)C.O1CCCC1.[CH2:13]([O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25](=[O:28])[CH2:26][Br:27])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(OCC)C.O>[CH2:13]([O:20][C:21]1[CH:30]=[CH:29][C:24]([C@H:25]([OH:28])[CH2:26][Br:27])=[CH:23][CH:22]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: -60 °C

Procedure

A mixture of 10.8 g of (L)-dibenzoylcystine, 1.6 g of lithium borohydride, 2.4 g of tert-butanol and 180 ml of tetrahydrofuran was refluxed for 1 hour and then cooled to -60° C. Thereto was added 6.1 g of 4-benzyloxyphenacyl bromide. The mixture was stirred for 30 minutes at the same temperature and further for 3 hours at -40° to -30° C. The reaction mixture was added to a mixture of 100 ml of water and 200 ml of diethyl ether. The organic layer was separated, washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography (eluant: toluene) to obtain 2.8 g of (S)-1-(4-benzyloxyphenyl)-2-bromoethanol.

Workup

temperaturewas refluxed for 1 hour
customThe organic layer was separated
washwashed with water
dry with materiala saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under reduced pressure
customThe residue thus obtained
customwas purified by column chromatography (eluant: toluene)

Sources & evidence

ORD record: ord-e1726396fe724200a47b7ecd77793cda
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872117

Reaction notes

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