Acetic Anhydride → HCID 54309198, compound

HRID 654956Notes

Reaction equation

HRID 654956 reaction equation
C([Li])CCC.[C:6]1([CH2:12][CH2:13][CH2:14][C:15]#[CH:16])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:17][Si:18]([CH3:27])([CH3:26])[C:19]1[O:23][CH:22]=[C:21](C=O)[CH:20]=1.[C:28]([O:31][C:32](=O)C)(=[O:30])[CH3:29]>CCCCCC.O1CCCC1.O>[C:28]([O:31][CH2:32][CH:16]([C:21]1[CH:20]=[C:19]([Si:18]([CH3:17])([CH3:26])[CH3:27])[O:23][CH:22]=1)[C:15]#[C:14][CH2:13][CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:30])[CH3:29]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 745735-Phenyl-1-pentyneHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 178418339Butyllithium

Product 1

HCID 54309198HCID 54309198, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (a 1.6M solution in hexane; 0.9 ml, 1.44 mmol) was added dropwise to a solution of 5-phenyl-1-pentyne (198.1 mg, 1.38 mmol) in tetrahydrofuran (4 ml) at 0° under argon. After 30 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (231 mg, 1.38 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 1 hour and acetic anhydride (0.4 ml) was added. After 2 hours, the mixture was poured into water and extracted thoroughly with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was flash chromatographed on silica using 5% ethyl ether/hexane. Fractions with Rf of about 0.33 on evaporation gave the title ester as an oil.

Workup

  1. waitwas continued for 1 hour
  2. waitAfter 2 hours
  3. extractionextracted thoroughly with ethyl ether
  4. customEvaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave an oil, which
  7. customchromatographed on silica using 5% ethyl ether/hexane
  8. customFractions with Rf of about 0.33 on evaporation

Sources & evidence

ORD record
ord-be2bcc0beb134ea18d5b078b71bb2c90
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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