Water → HCID 66777195, compound

HRID 2091092Notes

Reaction equation

HRID 2091092 reaction equation
[CH2:1]([CH:3]([CH2:17][CH3:18])[C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[BH4-].[Na+].O>CO.O1CCCC1>[CH2:17]([CH:3]([CH2:1][CH3:2])[CH:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:9]=2[C:10]=1[CH3:11])[OH:5])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 66777284HCID 66777284, compound

Product 1

HCID 66777195HCID 66777195, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Ethyl-1-(5-fluoro-3-methyl-1-benzofuran-2-yl)butan-1-one (15.0 g) synthesized above was dissolved in a mixed solvent of methanol (50 mL)-tetrahydrofuran (250 mL), and sodium tetrahydroborate (90%, 5.1 g) was added at 0° C. The reaction mixture was stirred at 0° C. for 1.5 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 (16.17 g, 100%) as a colorless 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-e0eaa04e98034bbf863451cb7ae6f21e
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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