Triethylamine → HCID 59317401, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 ml round bottom 3-neck flask equipped with a magnetic stirrer and nitrogen inlet was dissolved 3.58 g (11.1 mmol) 2-(hydroxymethyl)-4-methyl-6-(5-(trifluoromethyl)-2H-benzo[d][1,2,3]triazol-2-yl)phenol in 60 ml anhydrous THF. Triethylamine (5.6 ml, 40 mmol) was added and the mixture was cooled to −10° C. Methacryloyl chloride (1.373 g, 13.1 mmol) was added dropwise and the mixture was stirred for 1 hour at −10° C. followed by 20 hours at ambient temperature. The solid was filtered off and rinsed with diethyl ether and the resultant filtrate was poured into 100 ml diethyl ether and washed with 0.5 N HCl and water. The organic layer was dried with magnesium sulfate, filtered, and recrystallized with diethyl ether to give 1.90 g (44%) of a white solid. 1H NMR (CDCl3) delta: 11.17 (s, 1H, Ar—OH), 8.29 (s, 1H, Ar—H benzotriazole 4-position), 8.21 (s, 1H, Ar—H phenol 6-position), 8.06 (d, 1H, Ar—H benzotriazole 6-position), 7.69 (d, 1H, Ar—H benzotriazole 7-position), 7.29 (s, 1H, Ar—H phenol 4-position), 6.20 (s, 1H, C═C—H trans), 5.61 (s, 1H, C═C—H cis), 5.39 (s, 2H, Ar—CH2), 2.42 (s, 3H, Ar—CH3), 2.00 (s, 3H, C═C—CH3).

Provenance & Evidence