Methanol → HCID 131720615, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 250 mg (0.80 mmol) of (1) in 6 ml of dry dimethylformamide (Aldrich, 99%) was added 110 mg (0.80 mmol) of anhydrous potassium carbonate, followed by 109 ml (0.75 mmol) of ethyl-4-bromobutyrate and catalytic amount (4 mg) of 18-crown 6. The reaction mixture was heated at 120° C. for 2 h, cooled, and placed under reduced pressure to remove dimethylformamide. 50 ml of dichloromethane was added to the residue and the mixture was filtered. The filtrate was washed with 2×25 ml of 5% sodium hydroxide, brine, dried (anhydrous sodium sulphate) and concentrated. The residue was purified on preparative thin layer chromatography using a mixture of 6:1:1:1 ethyl acetate:methanol:water:concentrated ammonium hydroxide as the eluent and yielded 160 mg (0.37 mmol, 45%) of (5) as brown oil. MS, IR and NMR data confirmed the identity of the compound.

Provenance & Evidence