Chloromethyl Methyl Ether → HCID 86680616, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(4-(hydroxymethyl)phenyl)picolinaldehyde (0.6 g, 2.81 mmol) in DCM (15 mL) at 0° C. was added diisopropylethyl amine (1.5 mL, 8.4 mmol), followed by chloro(methoxy)methane (1.0 mL, 14.08 mmol). The reaction mixture was stirred at 0° C. for 3 h. After completion of the reaction by monitoring with TLC (30% EtOAc\hexane), the reaction mixture was extracted with dichloromethane (2×100 mL), washed with water (100 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by a Biotage Isolera® One column purifier (silica gel 100-200μ) using 13% ethyl acetate in hexane and the product isolated as a yellow viscous liquid (0.36 g, 50% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.14 (s, 1H), 8.32 (dd, 1H), 7.996 (d, 1H), 7.83 (d, 2H), 7.50 (d, 2H), 4.67 (s, 2H), 4.60 (s, 2H), 3.28 (s, 3H); LC-MS: m/z 258.1 [M+H]+.

Provenance & Evidence