Réaction #1552078

Équation de réaction

4-Isobutyl-1,6-dimethylcyclohex-3-enecarbaldehyde

MeMgBr

HCl

→

light yellow oil

Rendement 95.1%

1-(4-Isobutyl-1,6-dimethylcyclohex-3-enyl)ethanol

Rendement 95.1%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autreto rise to room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.STIRRINGAfter stirring for 10 min the phases
4. 4
   Autrewere separated
5. 5
   Extractionthe lower aqueous layer extracted twice with MTBE
6. 6
   Lavagewashed with sat. NaHCO3 solution and brine to pH 7
7. 7
   SéchageAfter drying (MgSO4) the organic phase
8. 8
   Concentrationwas concentrated in vacuo

Mode opératoire

4-Isobutyl-1,6-dimethylcyclohex-3-enecarbaldehyde 3c (4.5 g, 23 mmol) was dissolved in diethyl ether (40 ml). The solution was cooled to 0-5° C. under nitrogen and MeMgBr (3M, 12 ml, 35 mmol) added over 40 min with stirring. The temperature was allowed to rise to room temperature and stirring continued for 30 min. The reaction mixture was poured slowly onto a vigorously stirred mixture of 2M HCl and ice. After stirring for 10 min the phases were separated and the lower aqueous layer extracted twice with MTBE. The organic phases were combined and washed with sat. NaHCO3 solution and brine to pH 7. After drying (MgSO4) the organic phase was concentrated in vacuo to give 4.6 g of a light yellow oil. The crude oil was purified by flash chromatography (MTBE/hexane 3:7) to give 4d as a 1:2:3:5 mixture of diastereomers (2.7 g, 55% yield, >98% pure). Distillation of a 0.7 g sample gave 0.6 g of 4d (colorless oil, >99% pure) for olfactory assessment.

Source