1-(Thiophen-3-yl)ethanone → HCID 18936319, compound

HRID 2819Notes

Reaction equation

HRID 2819 reaction equation
C([Li])CCC.C[Si](C)(C)[C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[C:15]([C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)(=[O:17])[CH3:16].C(=O)([O-])O.[Na+]>C(OCC)C>[S:9]1[C:10]([C:15]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)([OH:17])[CH3:16])=[CH:11][N:12]=[CH:8]1

Participants

6

Reactant 4

HCID 151161-(Thiophen-3-yl)ethanoneHCID 516892Sodium BicarbonateHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 18936319HCID 18936319, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

n-Butyllithium (2.5M solution in hexane, 5.6 ml) in diethylether (25 ml) was stirred at -70° C. under a nitrogen atmosphere and 2-trimethylsilylthiazole (2 g) in diethylether (25 ml) was added dropwise. After 30 minutes 3-acetylthiophene (1.93 g) in diethylether (25 ml) was added dropwise. After a further 45 minutes the mixture was allowed to warm to room temperature and then left to stir for a further 1 hour. Saturated aqueous sodium hydrogen carbonate was added and the organic layer was separated. The aqueous layer was extracted with diethylether. The organic layers were combined, washed, dried and evaporated and the residue was purified by flash chromatography to give the title compound as an oil.

Workup

  1. waitleft
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with diethylether
  4. washwashed
  5. customdried
  6. customevaporated
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7674ce8e93ec4e02859f77b6a1662375
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Reaction notes

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