反応 #1552079

反応方程式

4-isobutyl-6-methylcyclohex-3-enecarbaldehyde

4-Isobutyl-6-methylcyclohex-3-enecarbaldehyde

EtMgBr

HCl

→

oil

収率 101.9%

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

収率 101.9%

溶媒

diethyl ether

反応条件

後処理

1. 1
   その他to 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
   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
7. 7
   その他to give a neutral pH
8. 8
   乾燥After drying (MgSO4) the organic phase
9. 9
   濃縮was concentrated in vacuo

実験手順

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).

出典