Pivalaldehyde → (NE)-N-(2,2-dimethylpropylidene)-2-methylpropane-2-sulfinamide

To a solution of pivalaldehyde (2 g, 2.56 ml, 23.2 mmol) in dry dichloromethane (150 mL) under argon atmosphere was added 2-methylpropane-2-sulfinamide (3.38 g, 27.9 mmol) and titanium (IV) ethoxide (6.36 g, 5.84 ml, 27.9 mmol) to give a colorless solution. The reaction mixture was stirred at r.t overnight and quenched by slow addition of water while the reaction still stirring until a precipitate formed. The reaction mixture was then filtered through a pad of celite. The filtrate was extracted with water, the organic phase was collected, dried over Na2SO4 and evaporated down in vacuo to give the title compound (3.6 gr, 82%) as crude oil. The crude was used without any further purification for the next step, MS (EI): m/e=190.3 [M+H]+.

1. customto give a colorless solution
2. customquenched by slow addition of water while the reaction
3. stirringstill stirring until a precipitate
4. customformed
5. filtrationThe reaction mixture was then filtered through a pad of celite
6. extractionThe filtrate was extracted with water
7. customthe organic phase was collected
8. dry with materialdried over Na2SO4
9. customevaporated down in vacuo

ORD record

ord-484be0bd693e4bc78b1b78c068d0073b

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290451B2