3,3-Dimethylglutaric anhydride → HCID 59511945, compound

Participants

Reaction Steps

Cool a solution of 3,3-dimethylglutaric anhydride (5.16 g, 36.3 mmol) in tetrahydrofuran to about 0° C. using an ice water bath. Add 3,4-(methlyeneoxy)phenylmagnesium bromide (1M solution in tetrahydrofuran, 40 mL, 40.0 mmol) quickly under a flow of nitrogen gas. Stir for 30 min, then allow to warm to room temperature over a period of 1 h. Quench with saturated ammonium chloride solution. Dilute with water and ethyl acetate, separate the aqueous layer (pH=8-9) and then acidify using 1N HCl (pH=4-5). Extract using ethyl acetate, dry with magnesium sulfate, filter, and concentrate to afford the crude title compound as an orange/yellow oil (5.99 g). Subject the crude residue to flash chromatography (RediSep silica gel columns (120 g), gradient of 100:0 to 75:25 cyclohexane/ethyl acetate) to obtain 1.80 g (19%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 7.58-7.61 (m, 1H), 7.45 (s, 1H), 6.82-6.87 (m, 1H), 6.05 (s, 2H), 3.00 (s, 2H), 2.52 (s, 2H) and 1.15 (s, 6H).

Provenance & Evidence