Water → HCID 66777218, compound

HRID 2091419Notes

Reaction equation

HRID 2091419 reaction equation
[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]4[CH2:25][CH2:24][CH2:23][O:22]4)=[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+].O>CO.O1CCCC1>[CH:1]1([CH:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH:21]4[CH2:25][CH2:24][CH2:23][O:22]4)=[CH:15][C:12]=3[C:13]=2[CH3:14])[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 66777063HCID 66777063, compound

Product 1

HCID 66777218HCID 66777218, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclohexyl[3-methyl-5-(tetrahydrofuran-2-ylmethoxy)-1-benzofuran-2-yl]methanone (260 mg) synthesized above was dissolved in methanol (0.5 mL)-tetrahydrofuran (2.5 mL), and sodium tetrahydroborate (90%) (64 mg) was added to the solution at 0° C. The reaction mixture was stirred at 0° C. for 2.5 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 (235 mg, 90%) as a colorless 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-f345990e52244cdb8ffd9b845e87242a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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