Sodium hydride → HCID 57493854, compound

N-(para-Toluenesulfonyl)dimethylsulfoximine (1.49 g, 6.01 mmol) and anhydrous DMSO (5 mL) were added to NaH 60% oil dispersion (0.22 g, 5.46 mmol) kept under stirring under anhydrous inert gas atmosphere in a flamed 3 necks flask. The mixture became greenish, and then changed to yellow. After stirring at 35° C. for 10 h, a solution of 4-methylidenecylohexanone (0.2 g, 1.82 mmol) in 5 mL of DMSO was added and the reaction mixture was stirred at 50° C. for 20 h. Afterwards, the reaction mixture was diluted with a saturated solution of NaCl and extracted with Et2O (3 times). After drying on Na2SO4 and evaporation to dryness, the residue from evaporation was purified by means of automated flash chromatography (Isolera®TM-Biotage; isocratic Petroleum Ether-EtOAc 9:1) to give 0.252 g of the title compound as a colorless oil. Yield: 27.8%.

1. temperaturea flamed 3 necks flask
2. stirringAfter stirring at 35° C. for 10 h
3. stirringthe reaction mixture was stirred at 50° C. for 20 h
4. extractionextracted with Et2O (3 times)
5. customAfter drying on Na2SO4 and evaporation to dryness
6. customthe residue from evaporation
7. customwas purified by means of automated flash chromatography (Isolera®TM-Biotage; isocratic Petroleum Ether-EtOAc 9:1)

ORD record

ord-6d56c59f150642c2aa8ca8d02ae219bb

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580962B2