Acetic Anhydride → 4-[1-Acetoxy-2-[3-(2-naphthyl)propoxy]ethyl]-2-trimethylsilylfuran

HRID 654961Notes

Reaction equation

HRID 654961 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.[C:45](OC(=O)C)(=[O:47])[CH3:46]>CCCCCC.O1CCCC1>[C:45]([O: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)(=[O:47])[CH3:46]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 67916977(2-Naphthyl)propyl tributylstannylmethyl etherHCID 178418339Butyllithium

Product 1

HCID 198859554-[1-Acetoxy-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; 0.69 ml, 1.1 mmol) was added dropwise to a solution of (2-naphthyl)propyl tributylstannylmethyl ether (511.9 mg, 1.05 mmol) in tetrahydrofuran (5 ml) at -78° under argon. After 5 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (176 mg, 1.05 mmol) in tetrahydrofuran (1/2 ml) was added, followed by acetic anhydride (0.1 ml, 1.58 mmol) after 25 minutes. Stirring was continued at -78° for 1 hour and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed using 10% ethyl ether/petroleum ether. The title ester was obtained as a pale yellow oil.

Workup

  1. waitwas continued at -78° for 1 hour
  2. customthe mixture was quenched with water
  3. extractionExtraction (ethyl ether) and evaporation of the
  4. dry with materialdried (magnesium sulphate)
  5. customextracts gave an oil, which
  6. customchromatographed

Sources & evidence

ORD record
ord-74cd7567e79744d8857324b441807050
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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