Thiophene → 1-(4-Methyl-5-oxazolyl)-1-(2-thienyl)ethanol

HRID 2807

反応式

HRID 2807 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[C:11]([C:14]1[O:18][CH:17]=[N:16][C:15]=1[CH3:19])(=[O:13])[CH3:12].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:19][C:15]1[N:16]=[CH:17][O:18][C:14]=1[C:11]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)([OH:13])[CH3:12]

参加物

6

反応物 4

HCID 8030ThiopheneHCID 516892Sodium BicarbonateHCID 110298391-(4-Methyloxazol-5-yl)ethanoneHCID 178418339Butyllithium

生成物 1

HCID 189363271-(4-Methyl-5-oxazolyl)-1-(2-thienyl)ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-40 °C

実験手順

Thiophene (3.36 g) in dry tetrahydrofuran (20 ml) was stirred and cooled to -40° C. under a dry nitrogen atmosphere and n-butyllithium (2.5M solution in hexane, 16 ml) was added dropwise. The mixture was allowed to warm to -20° C. and then after 1 hour was cooled to -70° C. 5-Acetyl-4-methyloxazole (5 g) in dry tetrahydrofuran (15 ml) was added dropwise. After a further 1 hour the mixture was allowed to warm the room temperature and was stirred for a further 2 hours. Aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The material thus obtained was purified by flash chromatography to give the title compound. M.p. 84°-85° C.

後処理

  1. temperatureto warm to -20° C.
  2. temperatureafter 1 hour was cooled to -70° C
  3. temperatureto warm the room temperature
  4. extractionthe mixture was extracted with diethylether
  5. customThe material thus obtained
  6. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-0cd8b984bb7449ec9670db072ec4ad56
出典データセット
uspto-grants-1998_03
特許番号
US05731335

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