Réaction #1552079

Équation de réaction

4-isobutyl-6-methylcyclohex-3-enecarbaldehyde

4-Isobutyl-6-methylcyclohex-3-enecarbaldehyde

EtMgBr

HCl

→

oil

Rendement 101.9%

1-(4-Isobutyl-6-methylcyclohex-3-enyl)propan-1-ol

Rendement 101.9%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autreto rise to room temperature
2. 2
   workup.STIRRINGthe reaction stirred for 10 min
3. 3
   workup.STIRRINGAfter stirring for 15 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
7. 7
   Autreto give a neutral pH
8. 8
   SéchageAfter drying (MgSO4) the organic phase
9. 9
   Concentrationwas concentrated in vacuo

Mode opératoire

4-isobutyl-6-methylcyclohex-3-enecarbaldehyde 3b (0.5 g, 2.8 mmol) was dissolved in diethyl ether (10 ml). The solution was cooled to 0-5° C. under nitrogen and EtMgBr (3M, 1.4 ml, 4.2 mmol) added over 10 min with stirring. The temperature was allowed to rise to room temperature and the reaction stirred for 10 min. The reaction mixture was poured slowly onto a vigorously stirred mixture of 2M HCl and ice. After stirring for 15 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 give a neutral pH. After drying (MgSO4) the organic phase was concentrated in vacuo to give 0.6 g of oil. The oil was purified by flash chromatography (MTBE/hex.1:4) to give 4e as a 2:85:8:4 mixture of diastereomers (0.54 g, 91% yield, colorless oil, >99% pure). Subsequent distillation provided an olfactory pure sample (0.4 g).

Source