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

HRID 1681441Notes

Reaction equation

HRID 1681441 reaction equation
[CH3:1][Si:2]([C:5]1[O:6][CH:7]=[C:8]([CH:10]=[O:11])[CH:9]=1)([CH3:4])[CH3:3].[BH4-].[Na+]>CO>[OH:11][CH2:10][C:8]1[CH:9]=[C:5]([Si:2]([CH3:4])([CH3:3])[CH3:1])[O:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethylsilyl-4-furaldehyde (Compound 10, 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 chromotography 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 chromotography on silica using 30% ethyl ether/hexane

Sources & evidence

ORD record
ord-aa307d0b80924a99ad3bd38a8481108c
Source dataset
uspto-grants-1992_12
Patent number
US05171864

Reaction notes

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