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

HRID 1681488Notes

Reaction equation

HRID 1681488 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 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-58876c2586544aceabecfe44cc2b2a06
Source dataset
uspto-grants-1992_12
Patent number
US05171863

Reaction notes

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