Sodium Carbonate → HCID 69838792, compound

Participants

Reaction Conditions

Reaction Steps

Sodium carbonate (0.72 g, 6.7 mmol) and 5% Pt/C (1.50 g, 75% weight of reactant) were added to a solution of (R)-6-chloro-8-difluoromethoxy-4-hydroxy-4-hydroxymethylthiochromane (2.0 g, 6.7 mmol; from step (v) above) in H2O (180 mL). The mixture was vigorously stirred at ca. 95° C. for 20-40 h with air being directly bubbled into the reaction mixture. The reaction was cooled to room temperature and filtered through a pad of Celite with saturated Na2CO3 solution (ca. 100 mL). The resulting liquid was slowly acidified with 2 N HCl (ca. 200 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with brine (75 mL), dried (Na2SO4), filtered, and concentrated in vacuo to afford 1.56 g (ca. 75%) of the sub-title compound as a brown oil which was used without further purification.

Provenance & Evidence