Sodium Iodide → HCID 69140908, compound

Participants

Reaction Conditions

Reaction Steps

To 500 mg (1.32 mmol) of 6 was added 10 ml of freshly distilled acetone (distilled over anhydrous K2CO3) and 10 ml of anhydrous DMF. To this reaction mixture was added 450 mg (3.0 mmol) of sodium iodide, 2 g of 4° A molecular sieves, 2 g (6.13 mmol) of cesium carbonate and a catalytic amount of 18-crown-6. To this reaction mixture was added 500 μl (3.38 mmol) of ethyl 4-bromobutyrate and the reaction mixture was heated on an preheated oil bath (90° C.) under argon atmosphere for 18 hours. The mixture was cooled to room temperature and filtered. The residue was washed with 30 ml of chloroform. The combined filtrate was concentrated under reduced pressure and redissolved in 100 ml of dichloromethane. This was washed with 2×100 ml of 5% NaOH followed by 2×100ml of water, dried (Na2SO4) and concentrated. The residue was purified by silica gel column chromatography using 10% methanol in dichloromethane to give 450 mg (1.09 mmol, 83%) of 7 as a brownish oil.

Provenance & Evidence