1-(Thiophen-3-yl)ethanone → 1-(5-Thiazolyl)-1-(3-thienyl)ethanol

HRID 975061Notes

Reaction equation

HRID 975061 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 189363191-(5-Thiazolyl)-1-(3-thienyl)ethanol

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-cac5ce3fe56c4f4ca6d36c22ccce9988
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Reaction notes

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