Toluene → HCID 13699158, compound

Temperature

0 °C

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.

1. dissolutionthe mixture was dissolved
2. temperaturereflux for 4 hr
3. customfor partitioning
4. washThe organic layer was washed with 5 w/w aqueous potassium hydrogen sulfate solution (85 mL)
5. washfurther washed twice with water (85 mL)
6. concentrationThe organic layer was concentrated under reduced pressure

ORD record

ord-21f4c468b8d44c7f9b8cf8aae893354f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238667B2