Reaktion #11308

Reaktionsgleichung

HCl

3-ethoxycyclohex-2-enone

phenylmagnesium bromide

→

title compound

3-phenylcyclohex-2-enone

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Sonstigeto quench
3. 3
   Sonstigethe reaction
4. 4
   Sonstigethe organic layer was separated
5. 5
   ExtraktionThe aqueous layer was extracted with dichloromethane 3 times
6. 6
   TrocknenThe combined organic layers were dried over magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

At 0° C., 3-ethoxycyclohex-2-enone (2 g, 14.3 mmol) in THF (2 mL) was added phenylmagnesium bromide (1.0 M solution in THF, 15.0 mL) slowly. After the addition, the reaction mixture was warmed up to room temperature and stirred for 1 hr. Then 1N HCl solution (15.16 mL) was added to quench the reaction and the organic layer was separated. The aqueous layer was extracted with dichloromethane 3 times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give the title compound as yellow solid (quantitative yield). 1H NMR (400 MHz, CDCl3) δ 2.16 (2H, dt, J=4, 12 Hz), 2.48 (2H, t, J=8 Hz), 2.77 (2H, dt, J=2, 6 Hz), 6.41 (1H, t, J=2 Hz), 7.39–7.41 (3H, m), 7.52–7.54 (2H, m).

Quelle