Cyclohexane → HCID 14502100, compound

Participants

Reaction Steps

A solution of 5 g (17.1 mmol) of methyl 2-methoxymethyloxy-3-allyl-4-acetylaminobenzoate in 20 ml of 1,4-dioxane is heated to 45° C. and 0.86 ml (6.86 mmol) of a 1M solution of osmium tetroxide in t-butanol is added in a single portion. Stirring is continued 15 minutes at 45° C. 7.32 g (34.2 mmol) of sodium periodate is added portionwise and stirring is continued 1 hour. Cyclohexane (1 ml) is added and stirring continued for 1 hour. The reaction mixture is then diluted with CH2Cl2 and washed with water. The organic layer is dried over MgSO4, filtered and concentrated. Flash chromatography (10% EtOAc/hexanes) affords pure 2-methoxymethyloxy-3-carbomethoxy-6-acetylaminophenylacetaldehyde which is used directly in the next step.

Provenance & Evidence