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

HRID 326375Notes

Reaction equation

HRID 326375 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-4c3b68022e4140e9b71f8f1fff530767
Source dataset
uspto-grants-1993_12
Patent number
US05268387

Reaction notes

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