Water → methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate

Participants

Reaction Steps

To a solution of methyl 3-(cyanomethyl)benzoate 1 (2 g, 11.4 mmol) in DMSO (20 mL) was added NaH (60%, 959 mg, 24.0 mmol) portion wise over 10 min. The reaction mixture was stirred for 40 min at rt and then bis(2-chloroethyl)ether (1.27 mL, 10.9 mmol) was added slowly and stirring continued for 18 hours. The reaction was poured into water and extracted with EtOAc/toluene (2:1). The combined extracts were washed with 2N HCl solution, water, brine, dried and evaporated the crude methyl 3-(4-cyanotetrahydro-2H-pyran-4-yl)benzoate 80 (1.25 g, 44%).

Provenance & Evidence