Réaction #1552076

Équation de réaction

MeLi

4-Isobutyl-6-methylcyclohex-3-enecarbaldehyde

NH4Cl

→

light yellow oil

Rendement 94.0%

1-(4-Isobutyl-6-methylcyclohex-3-enyl)ethanol

Rendement 94.0%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autreto rise to −5° C.
2. 2
   workup.STIRRINGthe reaction stirred at this temperature for 1 h
3. 3
   workup.ADDITIONThe reaction mixture was poured slowly
4. 4
   workup.STIRRINGAfter stirring for 15 min the phases
5. 5
   Autrewere separated
6. 6
   Extractionthe lower aqueous layer extracted with diethyl ether (100 ml)
7. 7
   Lavagewashed with water (100 ml)
8. 8
   Séchagedried (Na2SO4)
9. 9
   Concentrationconcentrated in vacuo

Mode opératoire

4-Isobutyl-6-methylcyclohex-3-enecarbaldehyde 3b (23 g, 130 mmol) was dissolved in diethyl ether (200 ml). The solution was cooled to −20° C. under nitrogen and MeLi (1.6M, 100 ml, 160 mmol) added over 30 min with stirring. The temperature was allowed to rise to −5° C. and the reaction stirred at this temperature for 1 h. The reaction mixture was poured slowly, and under nitrogen, onto a vigorously stirred mixture of sat. NH4Cl (150 ml) and ice (100 g). After stirring for 15 min the phases were separated and the lower aqueous layer extracted with diethyl ether (100 ml). The organic phases were combined, washed with water (100 ml), dried (Na2SO4) and concentrated in vacuo to give 24 g of a light yellow oil. The crude oil was purified by flash chromatography (MTBE/hexane 1:3) to give 4b as a 3:2 mixture of diastereomers (18 g, 72% yield, colorless oil, >99% pure). Subsequent distillation provided 12.5 g of olfactory pure product.

Source