Pyridine → 4-[2-(2,3-Dihydro-benzo[1,4]oxazin-4-yl)-ethoxy]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Preparation of 2-(2,3-dihydro-1,4-benzoxazine-4-yl)ethyl methanesulfonate--To a solution of 2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethanol (17.0 g, 94.9 mmol) in pyridine (200 ml) was added methanesulfonyl chloride (16.31 g, 142.0 mmol) dropwise at 0° C. The reaction mixture was stirred for 10 h at 25° C. Ice water (200 ml) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with 2N HCl (3×75 ml), water (75 ml), brine (50 ml) and dried (Na2SO4). The solvent was evaporated under reduced pressure. The residue was triturated with 5% ethyl acetate in pet. ether to afford the title compound (15.0 g, 61%) as brown solid. mp. 92-95° C.

Provenance & Evidence