Pyridine → HCID 54519927, compound

Pyridine (0.89 ml, 11.00 mmol) is added dropwise to a solution of chloromethyl chloroformate (1.32 ml, 14.83 mmol) and diethylene glycol (0.47 ml, 5.00 mmol) in dichloromethane (10 ml) at 7° C. with good stirring under a dry N2 atmosphere. After 10 min. at 7° C. and 6 hours at 20° C. the reaction mixture is transferred to a separating funnel with the aid of dichloromethane (10 ml). The reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (10 ml). The organic phase is dried (MgSO4) and the solvent evaporated under reduced pressure (10 mm Hg) to give 1.26 g (86%) title product. 1H NMR (300 MHz, CDCl3): δ 3.72 (m, 2×CH2 --O), 4.34 (m, 2×CH2 --O--C=O), 5.71 (s, 2×Cl--CH2 --O). 13C NMR (75 MHz, CDCl3): δ 67.6 (2×CH2 --O), 68.5 (2×CH2 --O--C=O), 72.1 (2×Cl--CH2 --O), 153.2 (2×C=O).

1. washThe reaction mixture is washed with hydrochloric acid (1.00M, 10 ml), saturated aqueous sodium hydrogen carbonate (10 ml) and water (10 ml)
2. dry with materialThe organic phase is dried (MgSO4)
3. customthe solvent evaporated under reduced pressure (10 mm Hg)

ORD record

ord-37a1135e7f2b4f469a6f80d5951a2ddf

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05534250