Reaktion #160798

Reaktionsgleichung

cyclohexene oxide

3-buten-1-ol

→

title compound

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed from the ice bath
2. 2
   SonstigeThe reaction was quenched with water
3. 3
   Extraktionextracted ether
4. 4
   WaschenThe combined organics were washed with brine
5. 5
   Sonstigedried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by column chromatography

Vorschrift

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).

Quelle