Sodium borohydride → Cyclohexyl(5,7-difluoro-3-methyl-1-benzofuran-2-yl)methanol

HRID 2091358Notes

Reaction equation

HRID 2091358 reaction equation
[CH:1]1([C:7]([C:9]2[O:10][C:11]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[CH:15][C:12]=3[C:13]=2[CH3:14])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>O1CCCC1.CO>[CH:1]1([CH:7]([C:9]2[O:10][C:11]3[C:18]([F:19])=[CH:17][C:16]([F:20])=[CH:15][C:12]=3[C:13]=2[CH3:14])[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66777401Cyclohexyl(5,7-difluoro-3-methyl-1-benzofuran-2-yl)methanone2×

Product 1

HCID 66777906Cyclohexyl(5,7-difluoro-3-methyl-1-benzofuran-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexyl(5,7-difluoro-3-methyl-1-benzofuran-2-yl)methanone (3.1 g) synthesized in the above-mentioned (1) was dissolved in tetrahydrofuran (50 mL) and methanol (5 mL), and sodium borohydride (90%, 0.93 g) was added to the solution under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hr then ice-cooled again, and water (5 mL) and 1N hydrochloric acid (10 mL) were carefully added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (3.1 g, quantitative) as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. customThe ice bath was removed
  3. temperatureice-cooled again
  4. additionwater (5 mL) and 1N hydrochloric acid (10 mL) were carefully added to the mixture
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)
  10. customto give the title object compound (3.1 g, quantitative) as a pale-yellow oil

Sources & evidence

ORD record
ord-81ac4f8ea46844f0ae424684ef81732e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…