Carbon Dioxide → HCID 15458596, compound

Participants

Reaction Steps

1.04 g (3.15 mmol) of 2,3-dimethyl-8-(1-hydroxy-2-[tert-butyldimethylsilyloxy]-1-hydroxy-ethyl)quinoline, 20 ml of ethyl ether and 0.53 ml (3.77 mmol) of triethylamine are introduced into a 100 ml round-bottomed flask. The mixture is cooled to −30° C. by a bath of cardice in acetone and 0.30 ml (3.9 mmol) of mesyl chloride are added. The cooling bath is removed and the reaction mixture is allowed to warm to room temperature over 30 minutes. 100 ml of water are added and the resulting mixture is extracted with ethyl ether (3×100 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is transferred, without further purification, into a 25 ml three-necked flask fitted with a condenser. 6.5 ml (63 mmol) of diethylamine and 5 ml of chloroform are added and this mixture is refluxed for 16 hours. The reaction mixture is cooled to room temperature and concentrated under vacuum, 50 ml of water are added and the resulting mixture is extracted with ethyl acetate (3×50 ml). The organic phases are combined, dried over magnesium sulphate and concentrated under vacuum. The residue is purified by chromatography on a column of silica (elution solvent: 10% methanol in dichloromethane). 0.64 g (yield: 53%) of 2,3-dimethyl-8-(1-diethylamino-2-[tert-butyldimethylsilyloxy]ethyl)quinoline is obtained in the form of an oil.

Provenance & Evidence