Aluminium lithium hydride → 3-(3',5'-Difluorobiphenyl-4-yl)propanoic acid

HRID 2410459Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25]C)=[O:24])=[CH:17][CH:16]=2)[CH:11]=[C:12]([F:14])[CH:13]=1>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:19][CH:20]=2)[CH:11]=[C:12]([F:14])[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of lithium aluminum hydride (0.2 g) in tetrahydrofuran (15 mL), the compound obtained from step c above (0.77 g) in tetrahydrofuran (50 mL) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was quenched carefully with saturated ammonium chloride solution, filtered through a celite pad, and washed with ethyl acetate. The organic layers were separated, washed with brine, and dried over anhydrous sodium sulfate, and solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash column chromatography using 20% to 30% ethyl acetate in hexane to get the title compound as a white crystalline solid (0.70 g).

Workup

customThe reaction mixture was quenched carefully with saturated ammonium chloride solution
filtrationfiltered through a celite pad
washwashed with ethyl acetate
customThe organic layers were separated
washwashed with brine
dry with materialdried over anhydrous sodium sulfate, and solvents
customwere evaporated under reduced pressure
customThe crude product was purified by silica gel flash column chromatography

Sources & evidence

ORD record: ord-c9f151ce99ae40648098500ece3bc20e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08816073B2

Reaction notes

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