5-(Trimethylsilyl)furan-3-carbaldehyde → HCID 19885919, compound

HRID 654903Notes

Reaction equation

HRID 654903 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]1[O:7][CH:6]=[C:5]([CH:8]=[O:9])[CH:4]=1.[CH2:12]([Li])[CH2:13][CH2:14][CH3:15]>O1CCCC1>[OH:9][CH:8]([C:5]1[CH:4]=[C:3]([Si:2]([CH3:11])([CH3:10])[CH3:1])[O:7][CH:6]=1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 19885919HCID 19885919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-trimethylsilyl-3-furaldehyde (0.134 g., 0.796 mmol) in 15 ml tetrahydrofuran at -78° under argon was added n-butyllithium (0.836 mmol in hexane). The reaction mixture was allowed to warm to room temperature, stirred for 30 minutes and quenched with a 5% ammonium chloride solution. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate solution. The organic portion was washed with water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol. This material was carried on without further purification.

Workup

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

Sources & evidence

ORD record
ord-056d8f8851664d4c8a463f7d8b94b85a
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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