5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione → HCID 86687583, compound

Participants

Reaction Conditions

Reaction Steps

To a vial charged with 3-bromo-4-methoxyaniline (1.207 g, 5.97 mmol) was added IPA (11.95 ml) and 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.112 g, 5.97 mmol) respectively. The mixture was heated to 90° C. for 2 hrs providing a brown solution which was cooled to room temp affording an orange precipitate which was collected by vacuum filtration affording 5-(((3-bromo-4-methoxyphenyl)amino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (1.8 g, 5.05 mmol, 85% yield). This solid was transferred to a 5-20 ml microwave vial and 10 ml (0.5M 1,2-dichlorobenzene) was added and the mixture irradiated at 225° C. for 15 mins affording conversion to desired product according to LC-MS. To the suspension was added diethyl ether (˜5 ml) to aid in product precipitation. To precipitate was collected via vacuum filtration and washed with ether, affording a brown solid as an isomeric mixture (˜10:1) (595 mg, 39%). m/z (ESI) 256.1 (M+H)+.

Provenance & Evidence