Sodium Chloride → N-cyclobutylidene-2-methylpropane-2-sulfinamide

Temperature

60 °C

2-methylpropane-2-sulfinamide (4.32 g, 35.7 mmol) and titanium(IV) ethoxide (16.3 g, 71.3 mmol) were added sequentially to a solution of cyclobutanone (2.5 g, 35.7 mmol) in THF (102 ml) at 22° C. The mixture was stirred at 60° C. for 5 h. The reaction mixture poured over a stirring saturated aqueous sodium chloride solution (60 mL). Celite was added to the suspension and it was filtered through a pad of Celite, washing with ethyl acetate (300 mL). The filtrate was washed with brine and the organic layers were combined and dried with anhydrous sodium sulfate. The dried solution was filtered and the filtrate was concentrated, yielding an oil which was purified on silica gel (Biotage, 25 g column, EtOAc/hexanes gradient, fraction collection at λ=254 nm) to give the expected product N-cyclobutylidene-2-methylpropane-2-sulfinamide (4.6 g, 27 mmol, 74% yield) consistent by NMR. 1H NMR (400 MHz, CHLOROFORM-d) δ 3.59-3.22 (m, 2H), 3.21-3.03 (m, 2H), 2.12 (t, J=8.2 Hz, 2H), 1.24 (s, 9H).

1. additionCelite was added to the suspension and it
2. filtrationwas filtered through a pad of Celite
3. washwashing with ethyl acetate (300 mL)
4. washThe filtrate was washed with brine
5. dry with materialdried with anhydrous sodium sulfate
6. filtrationThe dried solution was filtered
7. concentrationthe filtrate was concentrated
8. customyielding an oil which
9. customwas purified on silica gel (Biotage, 25 g column, EtOAc/hexanes gradient, fraction collection at λ=254 nm)

ORD record

ord-ac4a2964110447a696f127719edb5556

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962651B2