Borane;tetrahydrofuran → HCID 66649259, compound

HRID 469866Notes

Reaction equation

HRID 469866 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=[O:12])[C:8]([F:11])([F:10])[F:9].O1CCCC1.B>C1COCC1.Cl>[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([OH:12])[C:8]([F:10])([F:11])[F:9]

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 32983652-(Trifluoroacetyl)biphenyl

Product 1

HCID 66649259HCID 66649259, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-biphenyl-2-yl-2,2,2-trifluoro-ethanone (300 mg, 1.2 mmol), borane tetrahydrofuran complexes (1.2 ml, 1M in THF, 1.2 mmol) and S-2-methyl-CBS-oxazaborolidine (0.24 ml, 1M in toluene, 0.24 mmol) in THF (8 ml) was stirred at room temperature over night. Several drops of concentrated HCl were added and the mixture was stirred for 30 minutes. The product was purified by SiO2 chromatography (hexane/ethyl acetate=100/0 to 3/1) to give 290 mg of 1-biphenyl-2-yl-2,2,2-trifluoro-ethanol (96% yield).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe product was purified by SiO2 chromatography (hexane/ethyl acetate=100/0 to 3/1)

Sources & evidence

ORD record
ord-3461a3a3500c475189906dfcf1d22ab0
Source dataset
uspto-grants-2014_01
Patent number
US08629156B2

Reaction notes

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