Allyl Alcohol → Tetrahydrothiopyran-4-one-3-carboxylic acid

Participants

Reaction Steps

To a mixture of sodium hydride (60% in oil, 1.6 g, 38.7 mmol) in 10 mL of dry ether at room temperature was added allyl alcohol (2.25 g, 38.7 mmol) in a dropwise manner. The resultant mixture was stirred for 15 min. A solution of 3,3'-thiodipropionic acid, diallyl ester (5.0 g, 19.3 mmol) in 10 mL ether was slowly added and the mixture refluxed for 5 h. The reaction was cooled to room temperature and then quenched with water and the pH adjusted to 4 with 1N HCl. The ether layer was separated and the aqueous layer was extracted with ether (2×100 mL). The combined etheral layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue purified by flash column chromatography on silica gel eluted with hexane:ether (9:1) to give 2.57 g of tetrahydrothiopyran-4-one-3-carboxylic acid, allyl ester.

Provenance & Evidence