1,3,5-Trithiane → 2-{Bis(4-fluorophenyl)hydroxymethyl}-1,3,5-trithiane

Temperature

-60 °C

In 30 ml of anhydrous tetrahydrofuran was suspended 2.6 g of 1,3,5-trithiane, and 12 ml of 1.6M n-bytyl lithium was added dropwise under an argon atmosphere at a temperature of about -20° C. After completion of the dropwise addition, the resulting mixture was stirred for 2 hours. Next, the reaction mixture was cooled to about -60° C., and then a solution of 4.4 g of 4,4'-difluorobenzophenone dissolved in 100 ml of tetrahydrofuran was dropped thereinto. After completion of the dropping, the reaction temperature was slowly raised to 0° C. After stirring at 0° C. for another 1 hour, the reaction mixture thus obtained was poured into ice water and the resulting mixture was extracted with chloroform. The extract was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The crude product thus obtained was recrystallized from ether-hexane to give 5.58 g of the desired compound.

1. additionwas added dropwise under an argon atmosphere at a temperature of about -20° C
2. additionAfter completion of the dropwise addition
3. additionwas dropped
4. temperatureAfter completion of the dropping, the reaction temperature was slowly raised to 0° C
5. stirringAfter stirring at 0° C. for another 1 hour
6. customthe reaction mixture thus obtained
7. extractionthe resulting mixture was extracted with chloroform
8. washThe extract was washed with a saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous magnesium sulfate
10. customthe solvent was removed by distillation under reduced pressure
11. customThe crude product thus obtained
12. customwas recrystallized from ether-hexane

ORD record

ord-b504bba695ac49bbbb847108858f9d86

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05045562