Sodium Chloride → (4S,5E)-4-isopropyl-7-methylene-10-phenylthio-5-cyclodecen-1-one

Participants

Reaction Conditions

Reaction Steps

After dissolving 2.7 ml of hexamethyldisilazane (HMD) in 50 ml of dry tetrahydrofuran under argon gas stream, 7.3 ml of a 1.72N n-butyl lithium solution in n-hexane were added dropwise to prepare a lithium-bistrimethylsilylamide solution. After cooling the solution to -70° C., a solution of 2.0 g of the product of step 1, in 5 ml of dry tetrahydrofuran, was added dropwise under stirring and the resultant solution was agitated for 1 hour. The reaction mixture was added at once under agitation to a precooled (with ice) solution of 3.16 g of phenylthiobenzenesulfonate in 40 ml of dry tetrahydrofuran. After stirring the mixture for 10 minutes, 5 ml of a saturated sodium chloride aqueous solution were added to the reaction mixture, and this mixture was concentrated under reduced pressure. After adding 50 ml of water to the residue, the solution was extracted three times, each time with 50 ml of diethyl ether. The ether phases were combined, sequentially washed with water, a saturated sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated to dryness to provide (4S,5E)-4-isopropyl-7-methylene-10-phenylthio-5-cyclodecen-1-one the compound of formula 3).

Provenance & Evidence