반응 #1552081

반응 방정식

HCl

Pyridinium dichromate

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

PDC

→

3d

수율 77.0%

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

수율 77.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도cooled to below 5° C. under nitrogen
2. 2
   기타to return to room temperature
3. 3
   workup.ADDITIONwas added and after a further 90 min the reaction
4. 4
   workup.ADDITIONadded
5. 5
   추출After brief agitation the product was extracted from the aqeuous phase with MTBE
6. 6
   세척washed with sat. NaHCO3 solution
7. 7
   건조After drying (Na2SO4) the solvent
8. 8
   기타was removed in vacuo
9. 9
   기타to give 1.8 g of a crude oil which
10. 10
    기타was purified by flash chromatography (MTBE/hexane 2:8)

실험 절차

1-(4-Isobutyl-1,6-dimethylcyclohex-3-enyl)ethanol 4d (2 g, 9 mmol) was dissolved in dimethylformamide (50 ml) and cooled to below 5° C. under nitrogen. Pyridinium dichromate (4.5 g, 12 mmol) was added in two portions with stirring and the reaction allowed to return to room temperature. After stirring for 90 min another portion of PDC (1 g, 2.7 mmol) was added and after a further 90 min the reaction was complete. The reaction mixture was poured onto ice-water and 2M HCl added. After brief agitation the product was extracted from the aqeuous phase with MTBE. The organic phases were combined and washed with sat. NaHCO3 solution then to pH 7 with brine. After drying (Na2SO4) the solvent was removed in vacuo to give 1.8 g of a crude oil which was purified by flash chromatography (MTBE/hexane 2:8). Combination of pure fractions gave 3d as a 7:3 mixture of diastereomers (1.5 g, 77% yield, 99% pure). Subsequent distillation provided a sample for olfactory assessment.

출처