Pyridine → 1-Chloroethyl 1-methylethyl carbonate

Temperature

0 °C

To a solution of 1-chloroethyl carbonochloridate (10 g, 69.9 mmol) in DCM (200 mL) was added a solution of isopropanol (5.9 mL, 76.9 mmol) and pyridine (6.75 mL, 83.9 mmol) in DCM (50 mL) at −20° C. The reaction was stirred at 0° C. for 2 h, then at rt for another 2 h. The mixture was washed with 1N HCl solution (250 mL×2), followed by brine (250 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as colorless oil (9.6 g, 82.4%). The product was used in the next step without further purification. The title compound was characterized by 1H NMR as shown below:

1. waitat rt for another 2 h
2. washThe mixture was washed with 1N HCl solution (250 mL×2)
3. dry with materialThe organic phase was dried over anhydrous Na2SO4
4. concentrationconcentrated in vacuo

ORD record

ord-0fbe74fb87d048dc9976606d4dd3a28b

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399639B2