Water → HCID 11012298, compound

Participants

Reaction Steps

In a 200 ml Schlenk tube fitted with a septum, 6.97 g of crude product 3 and 4.35 ml (45 mmol) of triethylamine were dissolved in 100 ml of methylene chloride. At 0° C., 2.37 ml (31 mmol) of methanesulfonyl chloride were injected over a period of 2 minutes. After half the methanesulfonyl chloride had been added, a colorless precipitate formed. The suspension was held at this temperature for another half hour and was then stirred for 2 hours at room temperature. The reaction solution was subsequently hydrolyzed with 20 ml of water. The phases were separated and the aqueous phase was extracted three times with 20 ml of methylene chloride. The combined organic phases were washed with sodium chloride solution until neutral and dried over sodium sulfate. Removal of the solvent in an oil pump vacuum gave a slightly brownish oil which was dissolved in methylene chloride and absorbed on kieselguhr. This was followed by flash chromatography on a silical gel column (4*25 cm; PE/THF in a ratio of 8:2; RF =0.42). Evaporation of the product fractions in an oil pump vacuum gave 5.9 g (66%) of 4 as a colorless oil.

Provenance & Evidence