Hydrochloric Acid → HCID 86746898, compound

Participants

Reaction Steps

In 60 ml of anhydrous pyridine, 7.9 g of (3S, 4S)-5-hydroxy-3-methylpentan-4-olide (60.8 mmol) obtained in step [B] were dissolved. To the resultant solution, 15.1 g of tosyl chloride (79.0 mmol) were added with cooling by ice. The obtained mixture was stirred at room temperature overnight. The reacted solution was poured into a diluted hydrochloric acid solution which had been cooled, and extracted with methylene chloride. The obtained extract was washed with water and a saturated sodium chloride aqueous solution, in this order, and dried with anhydrous magnesium sulfate. Next, the obtained solution was filtered, and the obtained filtrate was concentrated. The obtained residue was purified via silica gel column chromatography (n-hexane:ethyl acetate=5:1 to 1:2) to obtain 14.8 g of (3S,4S)-3-methyl-5-tosyloxypentan-4-olide (tosylate) (yield: 85.5%). This product exhibited the following physical properties:

Provenance & Evidence