反応 #1552076

反応方程式

MeLi

4-Isobutyl-6-methylcyclohex-3-enecarbaldehyde

NH4Cl

→

light yellow oil

収率 94.0%

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

収率 94.0%

溶媒

diethyl ether

反応条件

後処理

1. 1
   その他to 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
   その他were separated
6. 6
   抽出the lower aqueous layer extracted with diethyl ether (100 ml)
7. 7
   洗浄washed with water (100 ml)
8. 8
   乾燥dried (Na2SO4)
9. 9
   濃縮concentrated in vacuo

実験手順

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.

出典