反応 #1552078

反応方程式

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

MeMgBr

HCl

→

light yellow oil

収率 95.1%

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

収率 95.1%

溶媒

diethyl ether

反応条件

後処理

1. 1
   その他to rise to room temperature
2. 2
   workup.STIRRINGstirring
3. 3
   workup.STIRRINGAfter stirring for 10 min the phases
4. 4
   その他were separated
5. 5
   抽出the lower aqueous layer extracted twice with MTBE
6. 6
   洗浄washed with sat. NaHCO3 solution and brine to pH 7
7. 7
   乾燥After drying (MgSO4) the organic phase
8. 8
   濃縮was concentrated in vacuo

実験手順

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.

出典