反应详情

温度

2 °C

10 kg tetrahydropyran-4-ol are dissolved in a mixture of 50 L toluene and 10.4 kg triethylamine. 11.55 kg methanesulfonyl chloride in 100 ml toluene are added while maintaining the internal temperature below 20° C. by cooling, and the addition funnel is rinsed with 50 ml toluene. The stirring is continued for one hour. The precipitate is filtered and the filter cake is washed twice with 20 L toluene each. The filtrate is concentrated by vaccum evaporation (60 L were distilled of), seeding crystals and 50 L methylcyclohexane are added. The suspension is cooled to 2° C. After 1 h the product is isolated by filtration, washed with 30 L methylcyclohexane and dried at 30° C. 16.6 kg of the product are obtained as a white solid. Yield: 94%; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62-1.73 (2H, m), 1.92-2.00 (2 H, m), 3.19 (3H, s), 3.42-3.49 (2H, m), 3.77-3.83 (2H, m), 4.80-4.88 (1H, m).

1. temperaturewhile maintaining the internal temperature below 20° C.
2. temperatureby cooling
3. washthe addition funnel is rinsed with 50 ml toluene
4. filtrationThe precipitate is filtered
5. washthe filter cake is washed twice with 20 L toluene each
6. concentrationThe filtrate is concentrated by vaccum evaporation (60 L were distilled of)
7. additionare added
8. customAfter 1 h the product is isolated by filtration
9. washwashed with 30 L methylcyclohexane
10. customdried at 30° C