Water → HCID 66777714, compound

HRID 2091406Notes

Reaction equation

HRID 2091406 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:18])=[C:14]([CH3:25])[C:13]=2[CH:26]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([CH:17]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[OH:18])=[C:14]([CH3:25])[C:13]=2[CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 66777037HCID 66777037, compound

Product 1

HCID 66777714HCID 66777714, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

[5-(Benzyloxy)-3-methyl-1-benzofuran-2-yl](cyclohexyl)methanone (23.4 g) synthesized in Example A82(2) was dissolved in methanol (40 mL)-tetrahydrofuran (400 mL), and sodium tetrahydroborate (90%) (5.64 g) was added to the solution at 0° C. The reaction mixture was stirred at 0° C. for 1 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 (25.17 g, 100%) 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-209847ada13842ce825009eab19b7a21
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

Loading…