Pyridine → Carbonic acid 1-chloroethyl ester (R)-1-methylbutyl ester

To a mixture of 1-chloroethyl chloroformate (1.19 mL), pyridine (1.49 mL), and THF (100 mL), (R)-(−)-2-pentanol [CSA No. 31087-44-2] (1 mL) dissolved in THF (3 mL) was added at −78° C. After stirring the mixture overnight at room temperature, ethyl acetate and heptane were added to the reaction mixture. The resulting mixture was sequentially washed with 0.5 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water, and saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure to obtain the captioned compound (1.8 g) as a crude product.

1. additionwas added at −78° C
2. washThe resulting mixture was sequentially washed with 0.5 N hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, water, and saturated aqueous sodium chloride solution
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationThe resulting mixture was filtered
5. customthe filtrate obtained
6. concentrationwas concentrated under reduced pressure

ORD record

ord-278f7c81a9bb4965b93b82b0fa33b030

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436009B2