Water → HCID 18925379, compound

HRID 1289057Notes

Reaction equation

HRID 1289057 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:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[CH3:16].O>C(OCC)C>[C:18]1([C:15]([C:10]2[S:9][CH:8]=[N:12][CH:11]=2)([OH:17])[CH3:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7410AcetophenoneHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 18925379HCID 18925379, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

n-Butyllithium (2.5M solution in hexane, 7ml) in diethyl ether (30ml) was stirred at -70° C. under a nitrogen atmosphere and 2-trimethylsilylthiazole (2.5g) in diethyl ether (10 ml) was added dropwise. After 30 minutes, acetophenone (2.3g) in diethyl ether (10 ml) was added dropwise. After a further 45 minutes the mixture was allowed to warm to room temperature and was then left overnight. Water was added and the mixture was extracted with diethyl ether. The material thus obtained was purified by flash chromatography to give the title compound.

Workup

  1. waitAfter a further 45 minutes the mixture was allowed
  2. waitwas then left overnight
  3. extractionthe mixture was extracted with diethyl ether
  4. customThe material thus obtained
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-567a965527c8438d813af234df0e8074
Source dataset
uspto-grants-1998_05
Patent number
US05747515

Reaction notes

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