Sodium borohydride → HCID 66777070, compound

HRID 2091331Notes

Reaction equation

HRID 2091331 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][CH2:21][S:22][CH3:23])=[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][CH2:20][CH2:21][S:22][CH3:23])=[CH:15][C:12]=3[C:13]=2[CH3:14])[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66777532HCID 66777532, compound2×

Product 1

HCID 66777070HCID 66777070, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclohexyl{3-methyl-5-[2-(methylsulfanyl)ethoxy]-1-benzofuran-2-yl}methanone (0.73 g) synthesized in the above-mentioned (1) was dissolved in a tetrahydrofuran (10 mL) and methanol (5 mL), and sodium borohydride (90%, 0.18 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. The mixture was ice-cooled again, water (1 mL) and 1N hydrochloric acid (5 mL) were carefully added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title object compound (0.67 g, 91%) as a pale-yellow oil.

Workup

  1. additionwas added to the solution under ice-
  2. temperaturecooling
  3. customThe ice bath was removed
  4. temperaturecooled again
  5. additionwater (1 mL) and 1N hydrochloric acid (5 mL) were carefully added
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record
ord-fbee63d3abf5420ba3c56ebd5358203f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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