3-Phenyl-2-triethylsilyl-4furaldehyde → 3-Phenyl-2-triethylsilyl-4-furanmethanol

HRID 1681528Notes

Reaction equation

HRID 1681528 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([C:13]2[C:17]([CH:18]=[O:19])=[CH:16][O:15][C:14]=2[Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1>[C:7]1([C:13]2[C:17]([CH2:18][OH:19])=[CH:16][O:15][C:14]=2[Si:20]([CH2:23][CH3:24])([CH2:25][CH3:26])[CH2:21][CH3:22])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 150371493-Phenyl-2-triethylsilyl-4furaldehydeHCID 21226445Aluminium lithium hydride

Product 1

HCID 150371503-Phenyl-2-triethylsilyl-4-furanmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.0M solution in hexane, 1.48 ml, 1.48 mmol) was added dropwise to a solution of 3-phenyl-2-triethylsilyl-4-furaldehyde (422 mg, 1.48 mmol) in tetrahydrofuran (10 ml) at 0 degrees under argon. This mixture was warmed to room temperature, quenched with ice-cold 5% (V/V) hydrochloric acid and the organics were extracted into ethyl ether. The combined fractions were washed with saturated sodium bicarbonate, H2O and brine. The dried extracts (magnesium sulfate) were concentrated to an oil which was purified by flash chromatography on silica using 20% ethyl acetate/hexanes to give the title compound.

Workup

  1. customquenched with ice-cold 5% (V/V) hydrochloric acid
  2. extractionthe organics were extracted into ethyl ether
  3. washThe combined fractions were washed with saturated sodium bicarbonate, H2O and brine
  4. concentrationThe dried extracts (magnesium sulfate) were concentrated to an oil which
  5. customwas purified by flash chromatography on silica using 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3c214e54b2af4188bb5ce83b614337b1
Source dataset
uspto-grants-1992_12
Patent number
US05171863

Reaction notes

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