反応 #2803

反応方程式

mesyl chloride

lithium chloride

2-(2-hydroxymethyl-phenyl)-ethanol

collidine

→

title compound

収率 45.0%

Methanesulfonic acid 2-(2-chloromethyl-phenyl)-ethyl ester

収率 45.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度Cool in an ice bath
2. 2
   その他partition between ice water (300 mL)
3. 3
   workup.ADDITIONa 1:1 mixture of ether
4. 4
   洗浄Wash the organic layer with a saturated solution of CuSO4 (2×200 mL)
5. 5
   乾燥dry (MgSO4)
6. 6
   その他purify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate)

実験手順

Mix 2-(2-hydroxymethyl-phenyl)-ethanol (12.0 g, 78.8 mmol) and collidine (23 mL, 0.17 mol) and treat with lithium chloride (7.35 g, 0.173 mmol) in dimethylformamide (125 mL). Cool in an ice bath and treat, by dropwise addition, with mesyl chloride (13.4 mL). Stir at 0° C. for 4 hours, partition between ice water (300 mL) and a 1:1 mixture of ether:pentane (2×400 mL). Wash the organic layer with a saturated solution of CuSO4 (2×200 mL), dry (MgSO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate) to give the title compound as a pale yellow oil (8.8 g, 45%).

出典