5-(Trimethylsilyl)furan-3-carbaldehyde → (2-Trimethylsilyl-4-furyl)methanol

HRID 654917Notes

Reaction equation

HRID 654917 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][Si:8]([CH3:17])([CH3:16])[C:9]1[O:13][CH:12]=[C:11]([CH:14]=[O:15])[CH:10]=1>O1CCCC1>[OH:15][CH2:14][C:11]1[CH:10]=[C:9]([Si:8]([CH3:17])([CH3:16])[CH3:7])[O:13][CH:12]=1

Participants

4

Reactant 2

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of lithium aluminum hydride (0.01 g., 0.263 mmol) in 1 ml dry tetrahydrofuran at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.09 g., 0.535 mmol). This mixture was allowed to warm to room temperature, stirred for 15 minutes, quenched with a 5% ammonium chloride solution, and extracted twice with ethyl ether. The organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol. This material was used without further purification.

Workup

  1. customquenched with a 5% ammonium chloride solution
  2. extractionextracted twice with ethyl ether
  3. washThe organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d2c4ff8f7014738b3f3a92e2fd781ca
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

Loading…