Water → HCID 136335136, compound

Participants

Reaction Steps

A solution of the product from Step A (6.99 g, 24.8 mmol) in a mixture of tetrahydrofuran (20 mL) and acetic acid (20 mL) was cooled in an ice bath. Sodium nitrite (5.13 g, 74.4 mol) was added and the mixture was stirred for one hour, warmed to room temperature and stirring continued for one hour. Water (200 mL) was added to the reaction mixture, which was extracted with ethyl acetate (200 mL). The organic layer was washed with aqueous saturated sodium bicarbonate (100 mL, to pH 7), dried (magnesium sulfate), filtered and saturated sodium bicarbonate (100 mL, to pH 7), dried (magnesium sulfate), filtered and evaporated to an oil (4.75 g). Purification by chromatography gave a bright yellow solid (2.96 g, 50%): mp 70–74° C.; LC/MS m/z 238.

Provenance & Evidence