N-Formylmorpholine → HCID 16110745, compound

Participants

Reaction Steps

Butyl lithium (20 mL, of 2.5M solution, 0.05 mol) at −78° C. over 15 minutes was added to a solution of Example 1B (11.8 g, 0.05 mol) in dry tetrahydrofuran. After one hour at the same temperature, formylmorpholine (5.8 g, 0.05 mol) was added drop wise and the mixture was stirred for 4 hours and then quenched with sat. NH4Cl. The aqueous layer was extracted with ethyl acetate and the organic phase washed with brine, dried over MgSO4 and filtered. The filtrate was concentrated and purified on silica gel (5˜35% ethyl acetate in hexane) to give 13.2 g of product as a yellow oil, 1H NMR (300 MHz, CDCl3) δ ppm 1.36 (d, J=5.88 Hz, 6H) 4.46-4.61 (m, 1H) 6.88-6.98 (m, 2H) 7.12-7.23 (m, 2H) 7.93 (s, 1H) 9.83 (s, 1H). MS (ESI), m/z 264.1 (M+H)+.

Provenance & Evidence