反应详情

A degassed solution of Bu3SnH (8.73 g, 30 mmol) in dry THF (40 ml) was added during 40 min to a degassed solution of methyl propynoate (2.52 g, 30 mmol) and Pd(PPh3)4 (0.693 g, 0.6 mmol) in THF (40 ml). The resulting mixture was stirred for 3.5 h at room temperature under nitrogen. THF was then removed under reduced pressure and the residue was diluted with hexane (200 ml). After 12 h, the mixture was filtered on celite and the filtrate was concentrated under reduced pressure. The residue was diluted with hexane (200 ml), filtered on celite and concentrated. The residue was purified by silica gel column using hexane/EtOAc (98/2) as eluant to give 4.7 g of 337B as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ 6.89 (d, J=2.64 Hz, 1H), 5.92 (d, J=2.64 Hz, 1H), 3.74 (s, 3H), 1.60-1.20 (m, 12H), 0.97 (t, J=8.34 Hz, 6H), 0.89 (t, J=7.03 Hz, 9H)

1. customTHF was then removed under reduced pressure
2. additionthe residue was diluted with hexane (200 ml)
3. waitAfter 12 h
4. filtrationthe mixture was filtered on celite
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionThe residue was diluted with hexane (200 ml)
7. filtrationfiltered on celite
8. concentrationconcentrated
9. customThe residue was purified by silica gel column