Ammonium Chloride → HCID 117759870, compound

HRID 1049611Notes

Reaction equation

[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][CH2:4][Mg]Cl.[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[C:19]([CH:34]=[O:35])=[CH:20][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:22][CH:23]=1.[Cl-].[NH4+]>C1COCC1>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=1[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:20][C:19]=1[CH:34]([OH:35])[CH2:4][CH2:3][C:2]([CH3:8])([CH3:7])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (3,3-dimethylbutyl)magnesium chloride in THF (0.50 M, 13.1 mL) was added to a solution of 2′-fluoro-5′-methoxy-4-((4-methoxybenzyl)oxy)-[1,1′-biphenyl]-2-carbaldehyde (800 mg) in THF (15 mL) at 0° C., and the mixture was stirred at 0° C. for 50 min. To the reaction mixture was added saturated aqueous ammonium chloride solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (788 mg) as a pale-yellow oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-8336a7f8b5604c4aa6fb7fe4bc580b19
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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