반응 #1552079

반응 방정식

4-isobutyl-6-methylcyclohex-3-enecarbaldehyde

4-Isobutyl-6-methylcyclohex-3-enecarbaldehyde

EtMgBr

HCl

→

oil

수율 101.9%

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

수율 101.9%

용매

diethyl ether

반응 조건

후처리

1. 1
   기타to 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
   기타were separated
5. 5
   추출the lower aqueous layer extracted twice with MTBE
6. 6
   세척washed with sat. NaHCO3 solution and brine
7. 7
   기타to give a neutral pH
8. 8
   건조After drying (MgSO4) the organic phase
9. 9
   농축was concentrated in vacuo

실험 절차

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).

출처