Dimethylformamide → HCID 90203154, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-methanesulfonyl-benzyloxy)-benzaldehyde oxime (4.65 g, 15.2 mmol; made using methods described in Example 2) in DMF (10 mL) was added N-chlorosuccinimide (2.60 g, 19.5 mmol) portionwise over 30 min. The mixture was then cooled to 0° C. after which it was allowed to return to rt and stirred for 1 h. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was evaporated to yield a white solid which was suspended in THF (60 mL). Ethyl 3-(1-pyrrolidino)-crotonate (3.65 g, 19.9 mmol) and triethylamine (4 mL, 28.7 mmol) in THF (20 mL) were added to the suspension. After stirring for 18 h at rt the reaction mixture was concentrated in vacuo and loaded directly onto silica gel. Chromatography (35% ethyl acetate in hexane) afforded 3-[4-(4-methanesulfonyl-benzyloxy)-phenyl]-5-methyl-isoxazole-4-carboxylic acid ethyl ester (2.39 g, 38%) as a clear oil that solidified into white disks.

Provenance & Evidence