反应 #452440

反应方程式

2-naphthoyl chloride

Lithium diisopropylamide

cis 3-Hexenyl acetate

→

desired product

cis 3-hexen-1-yl 3-(β-naphthyl)-3-oxo-propionate

溶剂

THF

THF

反应条件

后处理

1. 1
   其他fitted with a magnetic stirrer
2. 2
   workup.ADDITIONinternal thermometer, argon inlet, and addition funnel
3. 3
   workup.ADDITIONthe resulting solution added to the flask over 45 min
4. 4
   workup.ADDITIONOnce addition
5. 5
   workup.STIRRINGstirred at that temperature for 18 h
6. 6
   温度After warming to 0° C.
7. 7
   其他the mixture is quenched with 20% HCl (70 mL)
8. 8
   workup.ADDITIONThe mixture is poured into a separatory funnel
9. 9
   workup.ADDITIONcontaining ether (150 mL) and water (250 mL)
10. 10
    萃取The aqueous layer is extracted with ether (150 mL)
11. 11
    洗涤The combined organic layers are washed with saturated NaHCO3 solution (2×100 mL), water (2×150 mL) and brine (150 mL)
12. 12
    干燥dried over MgSO4
13. 13
    过滤filtered
14. 14
    其他The solvent is removed by rotary evaporation
15. 15
    其他to give an orange/red oil
16. 16
    其他The oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether)
17. 17
    其他to yield a colorless oil

实验过程

Lithium diisopropylamide (133.0 mL of a 2.0 M solution, 0.266 mol) is placed into a 500 mL three-necked round-bottomed flask fitted with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78° C. cis 3-Hexenyl acetate (17.80 g, 0.125 mol) is dissolved in THF (10 mL) and the resulting solution added to the flask over 45 min. Once addition is complete, the mixture is stirred for an additional 15 min. before being treated with a solution of 2-naphthoyl chloride (22.51 g, 0.118 mol) dissolved in THF (30 mL) over 30 min. The mixture is warmed to -20° C. and stirred at that temperature for 18 h. After warming to 0° C., the mixture is quenched with 20% HCl (70 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2×100 mL), water (2×150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to give an orange/red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether) to yield a colorless oil having 1H and 13C NMR spectra consistent with the desired product.

来源