Ammonium Chloride → HCID 11207006, compound

HRID 495694Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8](OC)=[O:9].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., a solution of 1.36 g (5.23 mmol) of methyl 3-fluoro-4′-methoxy-1,1′-biphenyl-4-carboxylate from Ex. V in 10 ml of anhydrous TMF is added dropwise to 3.14 ml (3.14 mmol) of a 1-molar solution of LiAlH4 in anhydrous THF. The mixture is initially stirred at 0° C. for 2 h. 10 ml of a sat. solution of NH4Cl are then added carefully, the mixture is diluted with ethyl acetate and the organic phase is separated off. The organic phase is washed successively with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and, after filtration, freed from the solvent. The resulting crude product is purified by flash chromatography (silica gel, cyclohexane/ethyl acetate 5:1). This gives 914 mg (3.94 mmol, 73% yield) of (3-fluoro-4′-methoxy-1,1′-biphenyl-4-yl) methanol.

Workup

customAt 0° C.
customthe organic phase is separated off
washThe organic phase is washed successively with water and saturated sodium chloride solution
dry with materialdried over anhydrous sodium sulfate
filtrationafter filtration
customThe resulting crude product is purified by flash chromatography (silica gel, cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record: ord-8b4478d8c31145968b734faaa76afe0b
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939989B2

Reaction notes

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