4-Toluenesulfonyl chloride → HCID 86607006, compound

Participants

Reaction Steps

A suspension of (R)-α-hydroxy-γ-butyrolactone (3.5 g, 34.3 mmol), tosyl chloride (10.0 g, 52.6 mmol), and K2CO3 (2.23 g, 16.2 mmol) in dry CH2Cl2 (50 mL) was stirred at room temperature overnight. The reaction mixture was filtered, and the filtrate washed with 1M phosphate buffer pH=7 (2×50 mL), 3 M NaCl (aq.) (1×50 mL), dried with Na2SO4, filtered and evaporated to dryness to give the crude product. The crude product was triturated by PE40/60 (50 mL) and stirred for 30 minutes. The precipitate formed was isolated by filtration and washed with PE40/60 to remove trace amounts of tosyl chloride, to give 7.7 g (87%) of enantiopure (R)-α-tosyloxy-γ-butyrolactone. [α]36525=−9.9°.

Provenance & Evidence