反応 #57403

反応方程式

water

2,2-Dimethyl-1-(1-naphthyl)-1,3-propanediol

triethylamine

Phosphorus oxychloride

→

title compound

収率 67.8%

2-Chloro-5,5-dimethyl-4-(1-naphthyl)-1,3,2-dioxaphosphorinane 2-oxide

収率 67.8%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise to the solution above
2. 2
   workup.STIRRINGThe solution was stirred at the same temperature for 1 hr
3. 3
   その他to partition
4. 4
   洗浄The organic layer was washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   濃縮concentrated under reduced pressure
7. 7
   workup.ADDITIONTo the obtained dark brown oil was added diethylether (100 ml) and diisopropylether (100 ml)
8. 8
   workup.STIRRINGthe mixture was stirred thoroughly
9. 9
   温度ice-cooled for 1 hr
10. 10
    workup.ADDITIONThe upper layer containing a large amount of unreacted 1-naphthoaldehyde
11. 11
    その他was removed by decantation
12. 12
    濃縮the under layer was concentrated

実験手順

2,2-Dimethyl-1-(1-naphthyl)-1,3-propanediol (83.6 g, 0.363 mol) and triethylamine (103.0 g, 1.018 mol) were dissolved in dichloromethane (300 ml). Phosphorus oxychloride (55.4 g, 0.361 mol) dissolved in dichloromethane (80 ml) was added dropwise to the solution above under cooling (2 to 4° C.) and with stirring for 1.5 hr. The solution was stirred at the same temperature for 1 hr, and water (150 ml) was added thereto to partition. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. To the obtained dark brown oil was added diethylether (100 ml) and diisopropylether (100 ml) and the mixture was stirred thoroughly and then ice-cooled for 1 hr. The upper layer containing a large amount of unreacted 1-naphthoaldehyde was removed by decantation and the under layer was concentrated to give the title compound as a black tar (76.1 g, yield 67.8%).

出典