反応 #359980

反応方程式

6-Dimethylamino-1-hexanol

Sodium hydride

2-methoxybenzyl chloride

→

O-(2-methoxybenzyl)-6-dimethylaminohexanol

収率 97.0%

溶媒

THF DMF

反応条件

後処理

1. 1
   温度the solution was cooled in an ice/water bath
2. 2
   workup.WAITAfter 3 h
3. 3
   その他the reaction was quenched by the addition of 1M NaHSO4
4. 4
   その他Tetrahydrofuran was removed in vacuo
5. 5
   洗浄the solution was washed with EtOAc
6. 6
   抽出extracted with ether
7. 7
   乾燥The combined ether phases were dried over K2CO3
8. 8
   ろ過filtered
9. 9
   その他the product was crystallized by the addition of 4M HCl/dioxane

実験手順

6-Dimethylamino-1-hexanol (8.80 g, 60.6 mmol) was dissolved in 2/1 mixture of THF/DMF (150 mL) and the solution was cooled in an ice/water bath. Sodium hydride (3.25 g, 80.8 mmol, 60% in oil) was added. After 40 min., 2-methoxybenzyl chloride (6.28 g, 40.4 mmol) was added and the solution was allowed to warm to room temperature over 1 h. After 3 h, the reaction was quenched by the addition of 1M NaHSO4. Tetrahydrofuran was removed in vacuo, and the solution was washed with EtOAc. The aqueous phase was basified with 3M NaOH and extracted with ether. The combined ether phases were dried over K2CO3, filtered, and the product was crystallized by the addition of 4M HCl/dioxane to give O-(2-methoxybenzyl)-6-dimethylaminohexanol (10.4 g) as a white solid.

出典