Triisopropyl phosphite → Ethyl 3-methylenecyclopentanecarboxylate

Temperature

100 °C

The following reaction was performed in a 15 mL sealed tube, behind a safety shield. To 2-((trimethylsilyl)methyl)allyl acetate (2.227 mL, 10.73 mmol) in toluene (2 mL) was sequentially added ethyl acrylate (2.92 mL, 26.8 mmol), triisopropyl phosphite (1.474 mL, 6.44 mmol) and palladium(II)acetate (0.241 g, 1.073 mmol). The contents were purged with nitrogen gas for 5 min. and heated at 100° C. for 45 h. The reaction mixture was cooled to RT and concentrated under reduced pressure. The liquid was transferred to a 50 mL round bottom flask and distilled using a high vacuum pump. Fractions distilling at 50° C. were collected and concentrated to yield 1.317 g (80%) of ethyl 3-methylenecyclopentanecarboxylate. 1H NMR (400 MHz, CDCl3) δ ppm 4.90-4.85 (m, 2H), 4.14 (q, 2H, J=7.0 Hz), 2.87-2.78 (m, 1H), 2.61-2.53 (m, 2H), 2.51-2.23 (m, 2H), 2.09-1.82 (m, 2H), 1.29-1.23 (t, 3H, J=7.2 Hz).

1. customThe following reaction
2. customsealed tube
3. customThe contents were purged with nitrogen gas for 5 min.
4. temperatureThe reaction mixture was cooled to RT
5. concentrationconcentrated under reduced pressure
6. customThe liquid was transferred to a 50 mL round bottom flask
7. distillationdistilled
8. distillationFractions distilling at 50° C.
9. customwere collected
10. concentrationconcentrated

ORD record

ord-ab341f62bd45439487fc214d214d21cc

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877749B2