Aluminium lithium hydride → HCID 67181670, compound

HRID 84045Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([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][CH:10]=1>O1CCCC1>[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of lithium aluminum hydride (2.28 g) in tetrahydrofuran (120 mL), the compound obtained from step c above (8 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 celite, 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 (5.1 g).

Workup

customThe reaction mixture was quenched carefully with saturated ammonium chloride solution
filtrationfiltered through celite
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-24393cda269944eb9b50dfa4d64bd181
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846910B2

Reaction notes

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