o-Toluenesulfonyl chloride → HCID 178424421, compound

Participants

Reaction Steps

Dried Compound 46 (29.24 g, 44.79 mmol) was dissolved in a mixture of anhydrous pyridine (82 mL) and anhydrous CH2Cl2 (82 mL). To this solution was added toluenesulfonyl chloride (21.3 g, 112 mmol). After stirring at room temperature for 10 hours, the mixture was poured into EtOAc (1 L), washed with saturated aqueous NaHCO3 (2×0.8 L), then with 1% (v/v) aqueous AcOH (2×0.8 L). Dried over anhydrous Na2SO4, filtered, and evaporated to a brown oil. Purification by silica gel chromatography (2:1 hexanes:EtOAc) yielded Compound 47 (32.36 g, 75%) as a pale yellow foam.

Provenance & Evidence