Réaction #160798

Équation de réaction

cyclohexene oxide

3-buten-1-ol

→

title compound

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

Conditions de réaction

Traitement

1. 1
   Autrewas removed from the ice bath
2. 2
   AutreThe reaction was quenched with water
3. 3
   Extractionextracted ether
4. 4
   LavageThe combined organics were washed with brine
5. 5
   Autredried
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   AutreThe residue was purified by column chromatography

Mode opératoire

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).

Source