Реакция #160824

Уравнение реакции

5-ethenyl-3,4-dihydro-2H-pyran

acrolein

water

→

title compound

(8R,8aR)-3,4,6,7,8,8a-hexahydro-2H-chromene-8-carbaldehyde

Растворители

CH2Cl2

Условия реакции

Обработка

1. 1
   Экстракцияextracted with CH2Cl2
2. 2
   ЭкстракцияThe crude extract
3. 3
   Фильтрацияwas filtered
4. 4
   Концентрированиеconcentrated
5. 5
   Другоеpurified on silica gel

Методика

A mixture of 2.613 g 5-ethenyl-3,4-dihydro-2H-pyran and 8.9 mL acrolein (90% pure) was dissolved in 39 mL CH2Cl2 and stirred overnight at RT. The reaction was added to water and extracted with CH2Cl2. The crude extract was filtered, concentrated using a rotovap, then purified on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ=1.64-1.98 (m, 5H), 2.04-2.16 (m, 1H), 2.23-2.29 (m, 1H), 2.34-2.38 (m, 1H), 2.60-2.64 (m, 1H), 3.55-3.61 in, 1H), 3.99-4.04 (m, 1H), 4.21 (d, J=5.6 Hz, 1H), 5.55 (s, 1H), 9.88 (s, 1H) ppm.

Источник