5-(Trimethylsilyl)furan-3-carbaldehyde → 4-[1-Hydroxy-2-[3-(2-naphthyl)propoxy]ethyl]-2-trimethylsilylfuran

HRID 654962Notes

Reaction equation

HRID 654962 reaction equation
C([Li])CCC.C([Sn]([CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1)(CCCC)CCCC)CCC.[CH3:34][Si:35]([CH3:44])([CH3:43])[C:36]1[O:40][CH:39]=[C:38]([CH:41]=[O:42])[CH:37]=1>CCCCCC.O1CCCC1>[OH:42][CH:41]([C:38]1[CH:37]=[C:36]([Si:35]([CH3:44])([CH3:43])[CH3:34])[O:40][CH:39]=1)[CH2:19][O:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:33]=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1

Participants

6

Reactant 3

HCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 67916977(2-Naphthyl)propyl tributylstannylmethyl etherHCID 178418339Butyllithium

Product 1

HCID 198859074-[1-Hydroxy-2-[3-(2-naphthyl)propoxy]ethyl]-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (a 1.6M solution in hexane; 0.56 ml, 0.94 mmol) was added dropwise to a solution of (2-naphthyl)propyl tributylstannylmethyl ether (437 mg, 0.89 mmol), prepared as in Example 3, in tetrahydrofuran (5 ml) at -78° under argon. After 5 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (150 mg, 0.89 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued at -78° for 2 hours and at room temperature for 1 hour. The mixture was quenched with water and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 30% ethyl ether/hexane. The title alcohol was obtained as a colorless oil.

Workup

  1. waitwas continued at -78° for 2 hours and at room temperature for 1 hour
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulphate)
  6. customextracts gave an oil, which
  7. customchromatographed on silica using 30% ethyl ether/hexane

Sources & evidence

ORD record
ord-344887a5410a4ac096c36f8a7441e477
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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