Pyridine → Chloromethyl isopropyl carbonate

Temperature

0 °C

Propan-2-ol (785 mg, 13.19 mmol) was added to a solution of chloromethyl chloroformate (1.7 g, 13.19 mmol) in dry ethyl ether (20 mL). The reaction mixture was cooled to 0° C. Pyridine (1.043 g, 13.19 mmol) was added dropwise with stirring. Thereafter, the reaction mixture was stirred at room temperature for 20 hours. The heterogenous mixture was filtered and the filtrate was washed with citric acid 1% (2×20 mL), NaHCO3 1% (2×20 mL) and brine (20 mL). The organic layer was dried over Na2SO4, filtered and evaporated to give desired compound (1.71 g, 85%). 1H NMR (CDCl3) δ: 5.69 (s, 2H, ClCH2O), 4.92 (sept, J=6.26 Hz, 1H, OCH(CH3)2), 1.30 (d, J=6.27 Hz, 6H, OCH(CH3)2). 13C NMR (CDCl3) δ: 152.68, 73.60, 71.95, 21.52 (2C).

1. stirringThereafter, the reaction mixture was stirred at room temperature for 20 hours
2. filtrationThe heterogenous mixture was filtered
3. washthe filtrate was washed with citric acid 1% (2×20 mL), NaHCO3 1% (2×20 mL) and brine (20 mL)
4. dry with materialThe organic layer was dried over Na2SO4
5. filtrationfiltered
6. customevaporated

ORD record

ord-1bb39fb678af42298fb668f209f60b62

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08884011B2