Tetrahydrofuran → (4'-Chlorobiphenyl-4-yl)(cyclohexyl)methanol

HRID 1520290Notes

Reaction equation

HRID 1520290 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1COCC1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]3)[OH:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 117839744(4'-Chlorobiphenyl-4-yl)(cyclohexyl)methanone

Product 1

HCID 117839871(4'-Chlorobiphenyl-4-yl)(cyclohexyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (4′-chlorobiphenyl-4-yl)(cyclohexyl)methanone (792.1 mg), THF (5.68 mL) and methanol (0.947 mL) was added sodium borohydride (120 mg) at 0° C. The reaction mixture was stirred at room temperature for 2 hr, and saturated aqueous sodium hydrogen carbonate solution was added at 0° C. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound as a crudely purified product. This compound was used in step C without further purification.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a6bd7cac52714ce9aeb31cb87b4ee629
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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