Triethylamine → Methanesulfonic acid 1-(3-methyl-pyridin-2-yl)-ethyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-methyl-pyridin-2-yl)-ethanol (330 mg, 2.41 mmol) (Kawasaki et al. Nippon Kagaku Zasshi 1962, 83, 949) and NEt3 (0.50 mL, 3.6 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. under N2. MsCl (0.22 mL, 2.8 mmol) was added and the reaction was stirred at 0° C. for 15 minutes. The reaction was diluted with saturated aqueous NaHCO3 (10 mL), the layers were separated and the aqueous solution was extracted with CH2Cl2 (10 mL×2). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure, giving the crude methanesulfonic acid 1-(3-methyl-pyridin-2-yl)-ethyl ester as an orange oil (484 mg, 2.25 mmol, 93%). 1H NMR (CDCl3) δ 1.76 (d, 3H, J=6.6 Hz), 2.45 (s, 3H), 2.84 (s, 3H), 6.07 (q, 1H, J=6.6 Hz), 7.20 (dd, 1H, J=7.8, 4.8 Hz), 7.51 (dd, 1H, J=7.8, 0.9 Hz), 8.51 (dd, 1H, J=4.8, 0.9 Hz).

Provenance & Evidence