Triethylamine → HCID 21997124, compound

Participants

Reaction Steps

To a stirred solution of 62.4 g (0.3 mol) of 4-tetrahydropyranyloxy benzyl alcohol and 58.5 mL of triethylamine in 225 mL of methylene chloride and 225 mL of diethyl ether cooled in an ice bath was added dropwise 31.9 mL (0.33 mol) of methacrylyl chloride at a rate such that the temperature did not exceed 30° C. After 3.5 hr, the mixture was filtered, and the filtrate was evaporated. The residual oil was treated with ether and triethylamine and washed with water. The organic layer was dried (sodium sulfate) and evaporated to a yellow oil, which, on standing, gradually crystallized. The crystals were rinsed with a small amount of methanol to give 7.3 g of colorless crystals, m.p. 36-36.7° C. The product can be recrystallized from hexane at low temperature. 1H NMR (360 MHz, THF-d8): 1.5-1.82 (m's, 6H, CH2), 1.90 (m, 3H, CH3C=), 3.5 (m, 1H, OCH 2), 3.8 (m, 1H, OCH2), 5.07 (s, 2H, ArCH2OOC), 5.40 (t, J=3, 1H, OCHO), 5.52 (m, 1H, =CH), 6.05 (m, 1H, =CH), 7.0 (m, 2H, ArH), 7.27 (m, 2H, ArH).

Provenance & Evidence