Sodium borohydride → 4-Hydroxymethyl-2-triethylsilylfuran

HRID 1109859Notes

Reaction equation

HRID 1109859 reaction equation
[BH4-].[Na+].[CH2:3]([Si:5]([CH2:15][CH3:16])([CH2:13][CH3:14])[C:6]1[O:7][CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[CH3:4]>CO>[OH:12][CH2:11][C:9]1[CH:10]=[C:6]([Si:5]([CH2:13][CH3:14])([CH2:15][CH3:16])[CH2:3][CH3:4])[O:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-

Product 1

HCID 150370354-Hydroxymethyl-2-triethylsilylfuran

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (353 mg, 0.93 mmol) was added portionwise to a solution of 2-triethylsilyl-4-furaldehyde (1.64 g, 7.79 mmol) in methanol (10 ml) at 0°. After 1 hour, most of the methanol was evaporated and the residue dissolved in a minimum amount of dilute hydrochloric acid. Extraction (ethyl acetate), drying (magnesium sulfate) and evaporation gave an oil, which was purified by flash chromatography on silica using 20% ethyl ether/hexane. Fractions with Rf of about 0.07 (10% ethyl ether/hexane) gave after evaporation the title alcohol as a colorless oil.

Workup

  1. custommost of the methanol was evaporated
  2. dissolutionthe residue dissolved in a minimum amount of dilute hydrochloric acid
  3. extractionExtraction (ethyl acetate)
  4. customdrying
  5. custom(magnesium sulfate) and evaporation
  6. customgave an oil, which
  7. customwas purified by flash chromatography on silica using 20% ethyl ether/hexane
  8. customFractions with Rf of about 0.07 (10% ethyl ether/hexane) gave
  9. customafter evaporation the title alcohol as a colorless oil

Sources & evidence

ORD record
ord-cdf6a767935e40828ff0dc08b7e51653
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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