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

HRID 1109899Notes

Reaction equation

HRID 1109899 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 (1.0 M 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 wtih 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. IR (neat): 3300 (broad); 2953 cm-1.

Workup

  1. customquenched wtih 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-2047d239c4774ec3860d1c2f0ef66211
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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