Reacción #2803

Ecuación de reacción

mesyl chloride

lithium chloride

2-(2-hydroxymethyl-phenyl)-ethanol

collidine

→

title compound

Rendimiento 45.0%

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

Rendimiento 45.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaCool in an ice bath
2. 2
   Otropartition between ice water (300 mL)
3. 3
   workup.ADDITIONa 1:1 mixture of ether
4. 4
   LavadoWash the organic layer with a saturated solution of CuSO4 (2×200 mL)
5. 5
   Secadodry (MgSO4)
6. 6
   Otropurify by silica gel chromatography (2.5:1 hexane/ethyl acetate followed by 2:1 hexane/ethyl acetate followed by 3:2 hexane/ethyl acetate)

Procedimiento

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%).

Fuente