Sodium borohydride → HCID 66778775, compound

HRID 2091374Notes

Reaction equation

HRID 2091374 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)=[O:11])=[C:7]([CH3:18])[C:6]=2[CH:19]=1.[BH4-].[Na+]>O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[OH:11])=[C:7]([CH3:18])[C:6]=2[CH:19]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 43805642HCID 43805642, compound2×

Product 1

HCID 66778775HCID 66778775, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(5-Bromo-3-methyl-1-benzofuran-2-yl)(cyclohexyl)methanone (7.5 g) synthesized in the above-mentioned (1) was dissolved in tetrahydrofuran (100 mL) and methanol (15 mL), and sodium borohydride (90%, 1.9 g) was added to the solution under ice-cooling. The ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hr then ice-cooled again, and water (10 mL) and 1N hydrochloric acid (50 mL) were carefully added to the mixture, 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 (7.4 g, quantitative) of the title object compound as a pale-yellow oil.

Workup

  1. temperaturecooling
  2. customThe ice bath was removed
  3. temperatureice-cooled again
  4. additionwater (10 mL) and 1N hydrochloric acid (50 mL) were carefully added to the mixture
  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-5a66b02c74f14ee6acbbf2bbc7a65843
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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