2-Phenyl-1,3-dithiane → HCID 19843053, compound

Temperature

-60 °C

To a solution of 2-phenyl-1,3-dithiane (6.4 g, 32.7 mmol) in tetrahydrofuran (100 mL) at -40° C. under argon atmosphere was added 2.5M n-butyllithium (13.1 mL, 37.7 mmol). After 30 minutes the temperature was adjusted to -20° C. and maintained for 1.5 hour. The temperature of the dark brown solution was lowered to -78° C. and but-4-yne (1.5 g, 14.9 mmol) was added neat. After 1 hour, the temperature was raised to -60° C. for 1.5 hour and the solution was then stored at -20° C. overnight. The reaction mixture was poured onto water, the layers separated, and the aqueous layer was back-extracted with methylene chloride (2×50 mL). The combined organic extracts were washed with brine, dried (MgSO4) and the solvents evaporated at reduced pressure to give the product as an oil.

1. temperaturemaintained for 1.5 hour
2. customwas lowered to -78° C.
3. waitAfter 1 hour
4. waitthe solution was then stored at -20° C. overnight
5. additionThe reaction mixture was poured onto water
6. customthe layers separated
7. extractionthe aqueous layer was back-extracted with methylene chloride (2×50 mL)
8. washThe combined organic extracts were washed with brine
9. dry with materialdried (MgSO4)
10. customthe solvents evaporated at reduced pressure

ORD record

ord-8c482e25bbc94bfbb982b174647dec37

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04877779