Triisopropyl phosphite → Ethyl 3-methylenecyclopentanecarboxylate

온도

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, 2 H), 4.14 (q, 2 H, J=7.0 Hz), 2.87-2.78 (m, 1 H), 2.61-2.53 (m, 2 H), 2.51-2.23 (m, 2 H), 2.09-1.82 (m, 2 H), 1.29-1.23 (t, 3 H, 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 기록

ord-df0acd41991d4285bb4731790b985848

출처 데이터셋

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09221819B2