Reacción #160798

Ecuación de reacción

cyclohexene oxide

3-buten-1-ol

→

title compound

2-(but-3-en-1-yloxy)cyclohexanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas removed from the ice bath
2. 2
   OtroThe reaction was quenched with water
3. 3
   Extracciónextracted ether
4. 4
   LavadoThe combined organics were washed with brine
5. 5
   Otrodried
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified by column chromatography

Procedimiento

To a mixture of cyclohexene oxide (3-1) (10.0 g, 102 mmol) in 3-buten-1-ol (17.4 mL, 204 mmol) cooled to 0° C. was added FeCl3 (1.65 g, 10.2 mol) The mixture was removed from the ice bath and stirred at rt for 1 hr. The reaction was quenched with water and extracted ether. The combined organics were washed with brine, dried, filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (400 MHz, CDCl3) δ 5.77-5.88 (m, 1H), 5.00-5.15 (m, 2H), 3.69-3.76 (m, 1H), 3.39-3.44 (m, 2H), 2.98-3.05 (m, 1H), 2.74 (s, 1H), 2.30-2.39 (m, 2H), 1.94-2.11 (m, 3H), 1.61-1.79 (m, 3H), 1.06-1.37 (m, 2H).

Fuente