反応 #350764

反応方程式

ammonium chloride

2-(3,4-diethoxyphenyl)-4-formylthiazole

1-bromo-3,4-dimethoxybenzene

→

2-(3,4-diethoxyphenyl)-4-[1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]thiazole

収率 48.9%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度cooling
2. 2
   workup.STIRRINGThe mixture was stirred at the same temperature for 1 hour and at room temperature for 3 hours
3. 3
   その他The solvent was removed by distillation
4. 4
   抽出The residue was extracted with 100 ml of chloroform
5. 5
   洗浄The extract was washed with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution
6. 6
   その他dried
7. 7
   その他The solvent was removed by distillation
8. 8
   その他The residue was purified by silica gel column chromatography (elutant: dichloromethane/acetone=99/1 by v/v)
9. 9
   その他recrystallized from diethyl ether

実験手順

60 ml of a tetrahydrofuran solution of a Grignard reagent prepared from 2.4 g of 1-bromo-3,4-dimethoxybenzene was stirred with ice-cooling. Thereto was added 20 ml of a tetrahydrofuran solution of 3 g of 2-(3,4-diethoxyphenyl)-4-formylthiazole. The mixture was stirred at the same temperature for 1 hour and at room temperature for 3 hours. 10 ml of a saturated aqueous ammonium chloride solution was added. The solvent was removed by distillation. The residue was extracted with 100 ml of chloroform. The extract was washed with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution, and dried. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (elutant: dichloromethane/acetone=99/1 by v/v) and recrystallized from diethyl ether to obtain 2.2 g of 2-(3,4-diethoxyphenyl)-4-[1-hydroxy-1-(3,4-dimethoxyphenyl)methyl]thiazole

出典