Water → HCID 86744625, compound

Participants

Reaction Conditions

Reaction Steps

Lithium azide (1.0 g, 20 mmol) is added to a solution of [1R,3S] 1-bromomethyl-3,4-dihydro-3-hydroxymethyl-5-methoxy-8-methyl-1H-2-benzopyran (1.77 g, 5.87 mmol), from Step 3, in 20 mL of DMF. The reaction mixture is heated to 70° C. for 1.5 h then cooled to ambient temperature and poured into 50 mL of diethyl ether and 50 mL of water. The layers are separated and the aqueous layer is extracted with 2×50 mL of diethyl ether. The combined ether layers are washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by column chromatography on silica gel to give the title compound.

Provenance & Evidence