Sodium Chloride → 2-Methyl-N-(oxetan-3-ylidene)propane-2-sulfinamide

Temperature

50 °C

Titanium (IV) ethoxide (0.25 mL, 1.2 mmol, 2.0 equiv) was added to a solution of oxetane-3-one (43 mg, 0.59 mmol, 1 equiv) and 2-methylpropane-2-sulfinamide (72 mg, 0.59 mmol, 1 equiv) in tetrahydrofuran (1.1 mL) at 22° C. The reaction mixture was heated to 50° C. for 16 hours, then was cooled to 22° C. and poured over stirring saturated aqueous sodium chloride solution (3 mL). The suspension was filtered through celite with the aid of ethyl acetate, and the filtrate was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over sodium sulfate, and the dried solution was filtered. The filtrate was concentrated to give 2-methyl-N-oxetan-3-ylidenepropane-2-sulfinamide (43 mg, 43%) as a light-yellow oil. Calc'd (M+1)+: 176.1. Found: 176.1.

1. temperaturewas cooled to 22° C.
2. additionpoured
3. filtrationThe suspension was filtered through celite with the aid of ethyl acetate
4. customthe filtrate was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
5. dry with materialThe organic layer was dried over sodium sulfate
6. filtrationthe dried solution was filtered
7. concentrationThe filtrate was concentrated

ORD record

ord-c89a520cded24f0bba965d3033c2192b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871796B2