تفاعل #359980

معادلة التفاعل

6-Dimethylamino-1-hexanol

Sodium hydride

2-methoxybenzyl chloride

→

O-(2-methoxybenzyl)-6-dimethylaminohexanol

المردود 97.0%

المذيبات

THF DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution was cooled in an ice/water bath
2. 2
   workup.WAITAfter 3 h
3. 3
   أخرىthe reaction was quenched by the addition of 1M NaHSO4
4. 4
   أخرىTetrahydrofuran was removed in vacuo
5. 5
   غسيلthe solution was washed with EtOAc
6. 6
   استخلاصextracted with ether
7. 7
   تجفيفThe combined ether phases were dried over K2CO3
8. 8
   ترشيحfiltered
9. 9
   أخرىthe product was crystallized by the addition of 4M HCl/dioxane

الإجراء التجريبي

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.

المصدر