1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-8-yl)-3,4-dihydro-2(1H)-quinazolinone → 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone

Participants

Reaction Steps

To a suspension of 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1,4-dioxaspiro(4.5)dec-8-yl)-3,4-dihydro-2(1H)-quinazolinone (248 mg, 0.456 mmol) (INTERMEDIATE 72) in acetone (12 mL) was added Amberlyst-15 (130 mg). The mixture was stirred at RT for 6 hours at which time the reaction mixture became homogeneous. The solution was filtered and the solvent concentrated. The crude material was purified by silica gel chromatography eluting with 1:4 acetone:hexanes followed by 1:3 acetone:hexanes to give 1-(2,6-Dichlorophenyl)-5-(2-chlorophenyl)-7-(1-cyclohexanon-4-yl)-3,4-dihydro-2(1H)-quinazolinone. 1H NMR (CDCl3, 500 MHz): selected data δ 1.78 (m, 2H), 2.14 (m, 2H), 2.4 (m, 4H) 2.86 (m, 1H). MS(ES) 499 (M+H); LC 1: 3.19 min.

Provenance & Evidence