Cyanogen Bromide → HCID 19874480, compound

Participants

Reaction Steps

A solution of cyanogen bromide (0.88 g) in methanol (100 ml) was added, dropwise, to a stirred solution of (4-acetonylphenoxy)-3-amino propan-2-ol), ethylene ketal (3.62 g) and sodium acetate (1.46 g) in methanol (30 ml). The reaction mixture was stirred at ambient temperature for 20 hr. evaporated, cooled in ice, diluted with 2N sodium hydroxide solution and extrated into chloroform. The organic layer was dried (MgSO4) and evaporated to an oil which was purified by column chromatography on silica gel. Elution with acetonitrile/methanol/ammonia (15:2:1) gave a low-melting solid which was dissolved in a mixture of methanol (30 ml) and 2N hydrochloric acid (30 ml) and stirred at ambient temperature for 4 hr. The methanol was evaporated and the aqueous residue was basified by addition of 2N sodium hydroxide solution, extracted into chloroform, dried (MgSO4) and evaporated to give 2-amino-5-(4-acetonylphenoxymethyl]-4,5-dihydrooxazole.

Provenance & Evidence