Chlorotrimethylsilane → 1-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

HRID 2816

反応式

HRID 2816 の反応式
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.C([Li])CCC.C[Si](Cl)(C)C.[C:17]([C:20]1[CH:24]=[C:23]([CH3:25])[O:22][C:21]=1[CH3:26])(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:26][C:21]1[O:22][C:23]([CH3:25])=[CH:24][C:20]=1[C:17]([C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1])([OH:19])[CH3:18]

参加物

7

反応物 5

HCID 6397ChlorotrimethylsilaneHCID 127484-MethylthiazoleHCID 615273-Acetyl-2,5-dimethylfuranHCID 516892Sodium BicarbonateHCID 178418339Butyllithium2 回

生成物 1

HCID 189362891-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-70 °C

実験手順

4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After 30 minutes the mixture was again cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes 3-acetyl-2,5-dimethylfuran (10 g) was added dropwise. The mixture was stirred at -70° C. for 1 hour and was then allowed to warm to room temperature. After 30 minutes, aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The combined extracts were washed, dried and evaporated to give the title compound which was recrystallised from diethylether. M.p. 100.5°-101.5° C.

後処理

  1. temperatureto warm to room temperature
  2. temperatureAfter 30 minutes the mixture was again cooled to -70° C.
  3. temperatureto warm to room temperature
  4. waitAfter 30 minutes
  5. extractionthe mixture was extracted with diethylether
  6. washThe combined extracts were washed
  7. customdried
  8. customevaporated

出典と根拠

ORDレコード
ord-01df543a66bb4268b36a7edbe14246e3
出典データセット
uspto-grants-1998_03
特許番号
US05731335

関連ノート

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