Diethyl Ether → HCID 89439926, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 5-bromonicotinaldehyde (0.5 g, 2.69 mmol), ethanesulfonamide (0.367 g, 3.36 mmol) and toluene (25 mL), then titanium tetra-isopropoxide (1.53 g, 5.38 mmol) was added dropwise. The reaction mixture was heated to 110° C. over night and then concentrated in vacuo. The residue was dissolved in THF (25 mL) and cooled down to −40° C. A 3 M solution of ethylmagnesium bromide in ether (2.24 mL, 6.72 mmol) was added dropwise at this temperature and the resulting mixture was slowly warmed up to −20° C. and stirred for 2.5 h. The mixture was poured into a saturated NH4Cl solution (15 mL), the resulting suspension was filtered and the filtrate was extracted with DCM (2×50 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.5 g, 56%) as light yellow oil. MS: 307.1 and 308.9.

Provenance & Evidence