Water → HCID 66777767, compound

HRID 2091098Notes

Reaction equation

HRID 2091098 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])=[C:11]([CH3:19])[C:10]=3[CH:20]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].O>CO.O1CCCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]3[O:13][C:12]([CH:14]([OH:18])[CH:15]([CH3:16])[CH3:17])=[C:11]([CH3:19])[C:10]=3[CH:20]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 66777957HCID 66777957, compound

Product 1

HCID 66777767HCID 66777767, compoundYield 113.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-[5-(Cyclopropylmethoxy)-3-methyl-1-benzofuran-2-yl]-2-methylpropan-1-one (19.91 g) synthesized above was dissolved in mixed solvent of methanol (40 mL)-tetrahydrofuran (200 mL), and sodium tetrahydroborate (90%, 5.53 g) was added at 0° C. The reaction mixture was stirred at 0° C. for 30 min. 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 (22.74 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-23471f63aa5a45cdaa86765637ae6427
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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