Acetic Anhydride → HCID 19885981, compound

HRID 654966Notes

Reaction equation

HRID 654966 reaction equation
C([Li])CCC.C([Sn]([O:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)(CCCC)CCCC)CCC.[CH3:29][Si:30]([CH3:39])([CH3:38])[C:31]1[O:35][CH:34]=[C:33](C=O)[CH:32]=1.[C:40]([O:43][C:44](=[O:46])[CH3:45])(=O)[CH3:41]>CCCCCC.O1CCCC1>[C:44]([O:43][CH:40]([C:33]1[CH:32]=[C:31]([Si:30]([CH3:39])([CH3:38])[CH3:29])[O:35][CH:34]=1)[CH2:41][O:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)(=[O:46])[CH3:45]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 67916865HCID 67916865, compoundHCID 178418339Butyllithium

Product 1

HCID 19885981HCID 19885981, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (a 1.6M solution in hexane; 0.46 ml, 0.74 mmol) was added dropwise to a solution of (2-pyridyl)propyl tributylstannyl ether (309.2 mg, 0.70 mmol) in tetrahydrofuran (5 ml) at -78° under argon. After 5 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (118 mg, 0.70 mmol) in tetrahydrofuran (1.5 ml) was added, followed by acetic anhydride (0.1 ml, 1.05 mmol) after 1 hour. Stirring was continued at -78° for 4 hours 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 on silica using 40% ethyl acetate/hexane. Fractions with Rf of about 0.12 on evaporation afforded the title ester as a yellow oil.

Workup

  1. waitwas continued at -78° for 4 hours
  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 on silica using 40% ethyl acetate/hexane
  7. customFractions with Rf of about 0.12 on evaporation

Sources & evidence

ORD record
ord-ed83b6738d4942efb5e8cb793182592a
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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