Chloride → HCID 86746132, compound

Temperature

-30 °C

To a solution of 1,3-dithiane (1.55 g, 12.9 mmole) in tetrahydrofuran (60 ml) cooled to -30° C. was added dropwise a 1.32M solution of n-butyllithium in hexane (9.77 ml, 12.9 mmoles), the mixture was stirred at -30° C. for 30 min. Then the mixture was cooled to -40° C. and the chloride prepared in 1C (2.69 g, 12.9 mmoles) in tetrahydrofuran (10 ml) was added dropwise. The reaction was stirred 30 min at -40° C. and 2 hrs at 0° C. The reaction was quenched with saturated aqueous ammonium chloride and the tetrahydrofuran was evaporated under reduced pressure. The residue was diluted with ether and washed with water. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography on silicagel and elution with a 8:2 mixture of hexane and ethyl acetate afforded the title dithialane as an oil (3.34 g, 90%). NMR (H1, CDCl3, 60 MHz) characetristic peaks: 4.00 (t, JHH =7 Hz, 1), 4.21 (d, JHF =20 Hz, 2), 4.7 (broad peak, 1), 5.40 (dt, JHF =20 Hz, JHH =8 Hz, 1).

1. temperatureThen the mixture was cooled to -40° C.
2. additionwas added dropwise
3. stirringThe reaction was stirred 30 min at -40° C. and 2 hrs at 0° C
4. customThe reaction was quenched with saturated aqueous ammonium chloride
5. customthe tetrahydrofuran was evaporated under reduced pressure
6. additionThe residue was diluted with ether
7. washwashed with water
8. dry with materialThe organic layer was dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. washFlash chromatography on silicagel and elution
12. additionwith a 8:2 mixture of hexane and ethyl acetate

ORD record

ord-5370ef45bd664bc680ae1b912ff0aa45

Source dataset

uspto-grants-1992_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05145861