Triethylamine → 1-(Pyrrolidin-1-yl)prop-2-en-1-one

Temperature

27.5 °C

To a stirred solution of pyrrolidine (2 g, 28.16 mmol) in anhydrous DCM (30 ml) was added triethylamine (15.56 ml, 111.88 mmol) and acryloyl chloride (3.04 g, 33.77 mmol) at 0° C. The reaction mixture was stirred at 20-35° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the reaction mixture was diluted with water (50 ml) and extracted with ethyl acetate (2×50 ml). The combined organic layers was washed with brine (50 ml), followed by drying over anhydrous Na2SO4 and filtering. The filtrate was rotary evaporated to get the desired compound as a brown liquid (1.1 g, 31%). 1H NMR (400 MHz, DMSO-d6) δ 6.49-6.33 (m, 2H), 5.66 (dd, J=9.8, 2.4 Hz, 1H), 3.54 (dt, J=6.8, 3.9 Hz, 4H), 2.02-1.91 (m, 2H), 1.90-1.82 (m, 2H).

1. stirringAfter 16 h of stirring
2. extractionextracted with ethyl acetate (2×50 ml)
3. washThe combined organic layers was washed with brine (50 ml)
4. dry with materialby drying over anhydrous Na2SO4
5. filtrationfiltering
6. customThe filtrate was rotary evaporated

ORD record

ord-cb9e0eb9e2bc4e8a875f23276359a996

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062002B2