(Diethylamino)sulfur trifluoride → HCID 9855696, compound

Temperature

-78 °C

To a round bottomed flask was added cis/trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (208 mg) and dichloromethane (3 ml). The resulting solution was cooled to −78° C., and diethylaminosulfur trifluoride (69 μl) added in one portion. The reaction mixture was allowed to warm to room temperature and stirred for 15 hr. The reaction mixture was partitioned between water (10 ml) and dichloromethane (20 ml), the layers were separated and the aqueous phase was extracted with dichloromethane (3×20 ml). The combined organic phases were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. The crude oil was dissolved in tetrahydrofuran (3 ml) and tetrabutylammonium fluoride (0.81 ml, 1.0M in tetrahydrofuran) and stirred at room temperature for 15 hr. The reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml) and the layers were separated. The aqueous phase was extracted with ethyl acetate (3×20 ml) and the combined organic phases were washed with brine (10 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 3:7 v/v) furnished the title compound (34 mg, 38%) as an off-white solid. δH (CD3OD): 1.69-1.86 (2H, m), 2.00-2.19 (4H, m), 3.09 (1H, tt), 5.67-5.80 (2H, m), 6.16 (1H, d), 6.20 (1H, dd), 6.91 (1H, d); m/z (ES−) 189 (M−H)+.

1. temperatureto warm to room temperature
2. customThe reaction mixture was partitioned between water (10 ml) and dichloromethane (20 ml)
3. customthe layers were separated
4. extractionthe aqueous phase was extracted with dichloromethane (3×20 ml)
5. washThe combined organic phases were washed with brine (20 ml)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. dissolutionThe crude oil was dissolved in tetrahydrofuran (3 ml)
10. stirringtetrabutylammonium fluoride (0.81 ml, 1.0M in tetrahydrofuran) and stirred at room temperature for 15 hr
11. customThe reaction mixture was partitioned between water (10 ml) and ethyl acetate (20 ml)
12. customthe layers were separated
13. extractionThe aqueous phase was extracted with ethyl acetate (3×20 ml)
14. washthe combined organic phases were washed with brine (10 ml)
15. dry with materialdried over magnesium sulfate
16. filtrationfiltered
17. concentrationconcentrated in vacuo
18. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 3:7 v/v)

ORD record

ord-2cde6bb5e0594c62904415ae8d43e4eb

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06797731B2