Chlorotrimethylsilane → 5-(Trimethylsilyl)furan-3-carbaldehyde

HRID 654890Notes

Reaction equation

HRID 654890 reaction equation
Br[C:2]1[O:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1.C([Li])(C)(C)C.[CH3:14][Si:15](Cl)([CH3:17])[CH3:16]>O1CCCC1>[CH3:14][Si:15]([CH3:17])([CH3:16])[C:2]1[O:6][CH:5]=[C:4]([CH:7]=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 150370565-Bromofuran-3-carbaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-bromo-3-furaldehyde, dimethyl acetal (1.26 g., 5.7 mmol) in 10 ml dry tetrahydrofuran at 78° under argon was added t-butyllithium (9.69 mmol in pentane), followed by the subsequent addition of trimethylsilyl chloride (1.36 g., 12.54 mmol). After two hours the reaction was quenched with a 10% ammonium chloride solution and the organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow oil. Purification by flash chromatography (10% ether/pet. ether) yielded the desired aldehyde.

Workup

  1. customAfter two hours the reaction was quenched with a 10% ammonium chloride solution
  2. washthe organic portion was washed with 5% sodium bicarbonate, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by flash chromatography (10% ether/pet. ether)

Sources & evidence

ORD record
ord-f09d0f6dd0cf41afaf26091bc5580437
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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