반응 #1552078

반응 방정식

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

MeMgBr

HCl

→

light yellow oil

수율 95.1%

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

수율 95.1%

용매

diethyl ether

반응 조건

후처리

1. 1
   기타to rise to room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.STIRRINGAfter stirring for 10 min the phases
4. 4
   기타were separated
5. 5
   추출the lower aqueous layer extracted twice with MTBE
6. 6
   세척washed with sat. NaHCO3 solution and brine to pH 7
7. 7
   건조After drying (MgSO4) the organic phase
8. 8
   농축was concentrated in vacuo

실험 절차

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.

출처