Water → HCID 66777773, compound

HRID 2091089Notes

Reaction equation

HRID 2091089 reaction equation
[CH:1]1([C:6]([C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([F:18])=[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[CH:17]=[CH:16][C:15]([F:18])=[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 46941771HCID 46941771, compound

Product 1

HCID 66777773HCID 66777773, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopentyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methanone (27.15 g) synthesized above was dissolved in a mixed solvent of methanol (40 mL)-tetrahydrofuran (240 mL), and sodium tetrahydroborate (90%, 5.5 g) was added 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 (29.26 g, 100%) as a yellow oil.

Workup

  1. additionwas added 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-e783e0b63e454b8193bf9bcbb20bd45c
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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