反応 #359978

反応方程式

2-methoxybenzyl chloride

6-(Dimethylamino)hexanol

Sodium hydride

water

→

O-(2-methoxybenzyl)-6-dimethylaminohexanol

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   温度the solution was cooled in an ice bath
2. 2
   その他was removed
3. 3
   workup.WAITAfter 4 h
4. 4
   その他the reaction mixture was quenched with 1 M sodium thiosulfate and tetrahydrofuran
5. 5
   その他was removed in vacuo
6. 6
   洗浄The reaction mixture was washed with ethyl acetate
7. 7
   抽出followed by extraction with ether
8. 8
   乾燥The ether layer was dried over potassium carbonate
9. 9
   ろ過filtered
10. 10
    濃縮The reaction mixture was concentrated in vacuo
11. 11
    その他the residue was crystallized form ethanol/ether

実験手順

6-(Dimethylamino)hexanol (8.80 g, 60.6 mmol) was dissolved in an anhydrous 2:1 mixture of tetrahydrofuran and dimethylfornamide (150 mL) and the solution was cooled in an ice bath. Sodium hydride (60% in oil, 3.23 g, 80.8 mmol) was added in portions and after 5 min. the water bath was removed. After 45 min., 2-methoxybenzyl chloride (6.28 g, 40.4 mmol) was added. After 4 h, the reaction mixture was quenched with 1 M sodium thiosulfate and tetrahydrofuran was removed in vacuo. The reaction mixture was washed with ethyl acetate and the aqueous phase was basified with 3 M sodium hydroxide, followed by extraction with ether. The ether layer was dried over potassium carbonate, filtered and acidified with 4 M hydrochloric acid in dioxane. The reaction mixture was concentrated in vacuo and the residue was crystallized form ethanol/ether to give O-(2-methoxybenzyl)-6-dimethylaminohexanol as the hydrochloride salt (10.4 g, 85%). MS (M-Cl)+266.3.

出典