Sodium borohydride → 2-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanol

HRID 2240964Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]=[C:6]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=2)[CH2:7]1)C.[BH4-].[Na+]>>[Br:16][C:12]1[CH:11]=[C:10]([CH:8]2[CH2:7][CH:6]([CH2:5][CH2:4][OH:3])[CH2:9]2)[CH:15]=[CH:14][CH:13]=1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 59790338HCID 59790338, compound

Product 1

HCID 593052992-[3-(3-Bromo-phenyl)-cyclobutyl]-ethanolYield 30.3%

Conditions

Temperature: 67 °C

Procedure

[3-(3-Bromo-phenyl)-cyclobutylidene]-acetic acid ethyl ester (1.96 gm, 6.63 mmol) was suspended in poly(ethylene glycol) (Average MW 400, 40 mL) and sodium borohydride (1.00 g, 26.4 mmol) was added portionwise. The slurry was warmed at 67° C. overnight, then cooled to room temperature and partitioned between 2N hydrochloric acid and diethylether. The ether extracts were dried with sodium sulfate and purified by column chromatography (50% EtOAc/hexanes) to afford 512 mg of an oil (30%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19-1.29 (m, 1H) 1.31-1.38 (m, 1H) 1.47-1.52 (m, 1H) 1.59-1.68 (m, 1H) 1.97-2.32 (m, 2H) 2.34-2.41 (m, 1H) 4.22-4.31 (m, 1H) 3.23-3.39 (m, 3H) 7.15-7.24 (m, 2H) 7.29-7.38 (m, 2H); MS (EI) m/z 254 [M+·].

Workup

temperaturecooled to room temperature
custompartitioned between 2N hydrochloric acid and diethylether
dry with materialThe ether extracts were dried with sodium sulfate
custompurified by column chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-ebc501d47dd944d59cd0e8c760aad825
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723368B2

Reaction notes

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