Reaktion #2803

Reaktionsgleichung

mesyl chloride

lithium chloride

2-(2-hydroxymethyl-phenyl)-ethanol

collidine

→

title compound

Ausbeute 45.0%

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

Ausbeute 45.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle