反応 #69930

反応方程式

cyclododecanone

THF

allyl magnesium bromide

→

alcohol

1-(2,3-Epoxypropyl)-cyclododecan-1-ol

反応条件

後処理

1. 1
   温度the flask was cooled in an ice bath for 10 minutes
2. 2
   その他was slowly dripped in over the course of 30 minutes
3. 3
   workup.ADDITIONAfter addition
4. 4
   その他the ice bath was removed
5. 5
   workup.STIRRINGthe reaction mixture was stirred for 4 hours at room temperature under nitrogen
6. 6
   その他Excess Grignard was quenched by slowly adding water to the reaction mixture
7. 7
   温度cooled to 0° C.
8. 8
   抽出the product was extracted three times with diethyl ether
9. 9
   乾燥The organic layer was dried over Na2SO4 and solvent
10. 10
    その他was removed under vacuum

実験手順

An oven-dried 500-mL three-neck round-bottom flask was charged with cyclododecanone (6.00 g, 32.9 mmol) and 50 mL dry THF. A 100-mL addition funnel with allyl magnesium bromide (1.0 M solution in THF, 36.2 mL, 36.2 mmol) was attached and the flask was cooled in an ice bath for 10 minutes. The Grignard was slowly dripped in over the course of 30 minutes while stirring at 0° C. under nitrogen. After addition, the ice bath was removed and the reaction mixture was stirred for 4 hours at room temperature under nitrogen. Excess Grignard was quenched by slowly adding water to the reaction mixture cooled to 0° C., and the product was extracted three times with diethyl ether. The organic layer was dried over Na2SO4 and solvent was removed under vacuum to obtain the homoallylic alcohol that was used without further purification.

出典