Sodium borohydride → (2-Trimethylsilyl-4-furyl)methanol

HRID 1736532Notes

Reaction equation

HRID 1736532 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:4][CH:5]=[C:6]([CH:8]=[O:9])[CH:7]=1.[BH4-].[Na+]>CO>[OH:9][CH2:8][C:6]1[CH:7]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:4][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 13333558(2-Trimethylsilyl-4-furyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Trimethylsilyl-4-furaldehyde (1.57 g, 9.35 mmol) was added to a suspension of sodium borohydride (424 mg, 11.2 mmol) in methanol (10 ml) at 0° C. After 45 minutes, most of the methanol was evaporated and the residue taken up in ethyl ether. The ethyl ether extracts were combined, washed (water), dried (magnesium sulfate) and evaporated to dryness to give an oil, which was purified by flash chromatography on silica using 30% ethyl ether/hexane to give the title alcohol as a pale yellow oil.

Workup

  1. custommost of the methanol was evaporated
  2. washwashed (water)
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated to dryness
  5. customto give an oil, which
  6. customwas purified by flash chromatography on silica using 30% ethyl ether/hexane

Sources & evidence

ORD record
ord-7c787720246d407ab26d8a156dba1fe3
Source dataset
uspto-grants-1996_07
Patent number
US05541221

Reaction notes

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