Water → HCID 66779078, compound

HRID 2091417Notes

Reaction equation

HRID 2091417 reaction equation
[CH:1]1([C:6]([C:8]2[O:9][C:10]3[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:11]=3[C:12]=2[CH3:13])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O>CO.O1CCCC1>[CH:1]1([CH:6]([C:8]2[O:9][C:10]3[C:17]([F:18])=[CH:16][C:15]([F:19])=[CH:14][C:11]=3[C:12]=2[CH3:13])[OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 66777910HCID 66777910, compound

Product 1

HCID 66779078HCID 66779078, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopentyl(5,7-difluoro-3-methyl-1-benzofuran-2-yl)methanone (1.24 g) synthesized above was dissolved in methanol (4 mL)-tetrahydrofuran (20 mL), and sodium tetrahydroborate (90%)(355 mg) was added to the solution at 0° C. The reaction mixture was stirred at 0° C. for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to give the title compound (1.18 g, 100%) as a yellow oil.

Workup

  1. additionwas added to the solution at 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-51e63cdc00934a9cae20f38a73934e7f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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