Reacción #969890

Ecuación de reacción

methane sulfonyl chloride

2-(5-ethyl-pyridine-2-yl)-ethanol

triethylamine

methane sulfonyl chloride

→

title compound

Methanesulfonic acid 2-(5-ethyl-pyridin-2-yl)-ethyl ester

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction stirred for 30 min
2. 2
   Lavadowashed with H2O and brine
3. 3
   SecadoThe organic layer was dried (MgSO4)
4. 4
   Concentraciónthe solution concentrated

Procedimiento

To a solution of 2-(5-ethyl-pyridine-2-yl)-ethanol (25.34 g) and triethylamine (46.7 mL) in DCM (130 mL) at 0° C. under nitrogen was added methane sulfonyl chloride (15.56 mL), then the reaction mixture was allowed to warm to room temperature and stirred overnight. A further portion of methane sulfonyl chloride (3.88 mL) was added and the reaction stirred for 30 min. The reaction was diluted with DCM and washed with H2O and brine. The organic layer was dried (MgSO4) and the solution concentrated to give the title compound as a red oil (38.24 g). 1H NMR (400 MHz, CDCl3): δ 8.39 (d, J=2.2 Hz, 1H), 7.47 (dd, J=7.7, 2.3 Hz, 1H), 7.14 (d, J=7.7 Hz, 1H), 4.64 (t, J=6.5 Hz, 2H), 3.19 (t, J=6.5 Hz, 2H), 2.90 (s, 3H), 2.64 (q, J=7.6 Hz, 2H), 1.25 (t, J=7.6 Hz, 3H).

Fuente