Sodium borohydride → HCID 66777014, compound

HRID 2091110Notes

Reaction equation

HRID 2091110 reaction equation
[CH:1]1([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]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+]>O1CCCC1.CO>[CH:1]1([CH:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19][CH:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)=[CH:15][C:12]=3[C:13]=2[CH3:14])[OH:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66777118HCID 66777118, compound2×

Product 1

HCID 66777014HCID 66777014, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexyl[3-methyl-5-(tetrahydro-2H-pyran-4-yloxy)-1-benzofuran-2-yl]methanone (7.1 g) synthesized in the above-mentioned (4) was dissolved in tetrahydrofuran (200 mL) and methanol (20 mL), and sodium borohydride (90%, 1.6 g) was added under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was ice-cooled again, water (10 mL) and 1N hydrochloric acid (100 mL) were added carefully, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a crude product (6.7 g, 98%) of the title object compound as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. customThe ice bath was removed
  3. temperaturecooled again
  4. additionwater (10 mL) and 1N hydrochloric acid (100 mL) were added carefully
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2db8f82a4c074706af574a6a9ad32325
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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