Sodium Azide → HCID 86609117, compound

Participants

Reaction Steps

A solution of [(2R)-8-(2,6-dichlorophenyl)-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate prepared in Example 35, step 7 (250 mg, 0.542 mmol) and sodium azide (141 mg, 2.17 mmol) in anhydrous dimethyl sulfoxide (10 mL) was heated at 70° C. under nitrogen for 20 hours. The cooled reaction mixture was quenched by the addition of water (20 mL) and the resulting suspension stirred vigorously for 5 minutes. The mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), the organic phase separated, washed with water (100 mL) and saturated brine (100 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 120 mg (67%) of (2R)-2-azidomethyl-8-(2,6-dichloro-phenyl)-2H-chromene as a colorless syrup that was used without further purification.

Provenance & Evidence