Triethylamine → (2-Chloropyridin-4-yl)methyl methanesulfonate

To a 0° C. solution of (2-chloro-pyridin-4-yl)-methanol (2.00 g, 13 mmol) (prepared from the corresponding carboxylic acid according to the procedure in U.S. Pat. No. 6,218,537), ethyl acetate (30 mL) and triethylamine (2.9 mL, 21 mmol) was added drop wise methansulfonyl chloride (1.4 mL, 18 mmol). The solution was stirred for 10 minutes and then water (5 mL) was added. The reaction mixture was extracted with three 30 mL portions of ethyl acetate, the organics combined and washed with water (30 mL) and brine (30 mL), dried on sodium sulfate, and concentrated to a crude oil. Pentane was added to the residue and stirred at 0° C. The precipitate was collected and dried in vacuo to give methanesulfonic acid 2-chloro-pyridin-4-ylmethyl ester (3.09 g, 100%).

1. extractionThe reaction mixture was extracted with three 30 mL portions of ethyl acetate
2. washwashed with water (30 mL) and brine (30 mL)
3. customdried on sodium sulfate
4. concentrationconcentrated to a crude oil
5. additionPentane was added to the residue
6. stirringstirred at 0° C
7. customThe precipitate was collected
8. customdried in vacuo

ORD record

ord-31704c4e0c9d4be997a6005f79446e78

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759428B2