Tetramethylammonium fluoride → HCID 67060889, compound

Temperature

-35 °C

2-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide (100 mg, 0.571 mmol) was dissolved in THF (2 mL). The solution was cooled down to −35° C. and added tetramethylammonium fluoride (63.8 mg, 0.685 mmol). The mixture was degassed and charged with argon. Trimethyl(trifluoromethyl)silane (0.134 ml, 0.856 mmol) in THF (1 mL) was added slowly via syringe. The reaction was stirred at this temperature for 2 h, warmed to −10° C. and quenched with saturated aqueous NH4Cl solution. The mixture was extracted with ethyl acetate, dried over anhydrous Na2SO4, and concentrated. The residue was purified by column chromatography to give the title compound (53 mg). LCMS m/z=246.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 1.29 (s, 9H), 3.79 (s, 1H), 4.78-4.85 (m, 3H), 4.98 (dd, J=7.6 and 1.3 Hz, 1H).

1. customThe mixture was degassed
2. additioncharged with argon
3. temperaturewarmed to −10° C.
4. customquenched with saturated aqueous NH4Cl solution
5. extractionThe mixture was extracted with ethyl acetate
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated
8. customThe residue was purified by column chromatography

ORD record

ord-7ad1d1d800eb4e8e90521a38162110bc

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778950B2