Sodium Hydroxide → HCID 25183506, compound

Participants

Reaction Steps

A solution of 154 (172 mg; 0.43 mmol) in tetrahydrofuran (2.1 mL) was placed in a 2.5-5.0 mL microwave reactor tube. Aqueous sodium hydroxide (2.1 mL; 2N) was added and the reaction vessel was subjected to the following microwave conditions: Temperature=140° C.; Time=30 minutes; Power=250 W; Cooling on; Absorption=High. After cooling to room temperature, the reaction mixture was acidified with aqueous hydrochloric acid (25 mL; 6N) and extracted with ethyl acetate (40 mL×2). The organic layers were combined and successively washed with aqueous sodium hydroxide (20 mL; 2N), aqueous hydrochloric acid (25 mL; 6N), and aqueous saturated sodium chloride (25 mL). The dichloromethane extracts were dried over magnesium sulfate, filtered, and concentrated under reduced. The resulting white solid was purified by silica gel chromatography (2 columns; 1st column gradient: 16% ethyl acetate in hexanes to 5% methanol in dichloromethane; 2nd column gradient: dichloromethane to 5% methanol in dichloromethane) to yield the title compound as a white solid (61 mg).

Provenance & Evidence