Toluene → HCID 13699158, compound

Participants

Reaction Conditions

Reaction Steps

Into a 500 mL four neck flask were added 2-pyrrolidone (17.02 g) [mw. 85.10, 200 mmol] and toluene (340 mL), and the mixture was dissolved. Powder sodium hydroxide (8.00 g) [mw. 40.00, 200 mmol] was added thereto, Dean-Stark trap was set, and the mixture was subjected to dehydration reflux for 4 hr. After cooling to 0° C., allyloxycarbonyl chloride (20.10 g) [mw. 120.53, 167 mmol] was added at not more than 30° C., and the mixture was stirred at 25° C. for 30 min. Water (85 mL) and tetrahydrofuran (85 mL) were added to allow for partitioning. The organic layer was washed with 5 w/w aqueous potassium hydrogen sulfate solution (85 mL), and further washed twice with water (85 mL). The organic layer was concentrated under reduced pressure, and the solvent was replaced with tetrahydrofuran. Pale-yellow oil, 19.28 g, yield 57.0%, 1H-NMR (500 MHz, CDCl3, TMS) δ 2.09 (quin, J=7.7 Hz, 2H), 2.54 (t, J=8.2 Hz, 2H), 3.80-3.86 (m, 2H), 4.70-4.77 (m, 2H), 5.25-5.38 (m, 1H), 5.38-5.45 (m, 1H), 5.88-6.04 (m, 1H). 13C-NMR (125 MHz, CDCl3, CDCl3) δ 17.57, 32.78, 46.42, 66.87, 118.76, 131.57, 151.38, 173.98.

Provenance & Evidence