반응 #160815

반응 방정식

tetrahydro-4H-pyran-4-one

prop-2-en-1-ol

Xantphos

DL-proline

→

title compound

3-(prop-2-en-1-yl)tetrahydro-4H-pyran-4-one

용매

DMSO

반응 조건

후처리

1. 1
   기타was degassed (2×pump/N2)
2. 2
   온도The mixture was cooled to rt
3. 3
   기타partitioned between water and Et2O
4. 4
   추출Extracted with Et2O
5. 5
   세척The combined organics were washed with 1:1 brine
6. 6
   건조water, dried (anhd. Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated
9. 9
   기타The residue was purified by column chromatography

실험 절차

A mixture of tetrahydro-4H-pyran-4-one (6-1) (5.17 g, 51.7 mmol), prop-2-en-1-ol (1.00 g, 17.2 mmol), allylPalladium Chloride dimer (0.157 g, 0.430 mmol), Xantphos (0.498 g, 0.861 mmol), and DL-proline (0.595 g, 5.17 mmol) in DMSO (35 mL) was degassed (2×pump/N2) and heated to 70° C. overnight. The mixture was cooled to rt and partitioned between water and Et2O. Extracted with Et2O. The combined organics were washed with 1:1 brine:water, dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.70-5.80 (m, 1H), 5.01-5.09 (m, 2H), 4.13-4.22 (m, 2H), 3.72-3.79 (m, 1H), 3.43 (t, 1H, J=11.2 Hz), 2.52-2.66 (m, 3H), 2.39-2.47 (m, 1H), 1.99-2.07 (m, 1H).

출처