反应详情

温度

5 °C

Into a 2000 ml three-neck flask having a thermometer, a cooler, a stirring device, and a dripping funnel, 190.65 g (1.0 mol) of p-toluene sulfonate chloride, 32.24 g (0.1 mol) of tetramethylammonium bromide, and 400 ml of toluene were poured and cooled to 5° C. with stirring in an ice bath. After pouring 116.16 g (1.0 mmol) of 3-ethyl-hydroxymethyloxetane into the three-neck flask, 130 ml of a 35 wt % sodium hydroxide solution was dripped into the three-neck flask in 30 minutes. After the dripping, stirring was continued for 1 hour at the same temperature and then for 16 hours at a room temperature. After the reaction, 800 ml of water was poured into the flask followed by violent stirring. The mixture was left to stand to separate a water phase from an organic phase. The organic phase was washed with 400 ml of water and then dried with anhydrous magnesium sulfate over night. Then, the magnesium sulfate was removed by filtration, and the filtrate was concentrated. The thus-obtained crude product was separated and purified by silica gel column chromatography (eluting solution: hexane/ethyl acetate) to obtain a desired substance, i.e. 243.3 g (yield: 90%) of 2-(3-oxetanyl)butyltosylate as a colorless liquid.

1. customInto a 2000 ml three-neck flask having
2. stirringAfter the dripping, stirring
3. waitwas continued for 1 hour at the same temperature
4. waitfor 16 hours at a room temperature
5. additionwas poured into the flask
6. waitThe mixture was left
7. customto separate a water phase from an organic phase
8. washThe organic phase was washed with 400 ml of water
9. dry with materialdried with anhydrous magnesium sulfate over night
10. customThen, the magnesium sulfate was removed by filtration
11. concentrationthe filtrate was concentrated
12. customThe thus-obtained crude product
13. customwas separated
14. custompurified by silica gel column chromatography (eluting solution: hexane/ethyl acetate)