Nitric Acid → 5-nitrooxypentanoic Acid

反応式

S(=O)(=O)(O)O.[N+:6]([O-:9])([OH:8])=[O:7].Br[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]>ClCCl>[N+:6]([O:9][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])([O-:8])=[O:7]

参加物

反応条件

温度: 0 °C

実験手順

Concentrated sulphuric acid 96% (1.24 mL, 2.0 eq) was added dropwise to fuming nitric acid 100% (0.97 mL, 2.0 eq) at 0° C. After 10 minutes of stirring at 0° C., a solution of 1 (2.00 g, 1.0 eq) in dichloromethane (20.0 mL) was added dropwise. The reaction mixture was stirred from 0° C. to RT for 3 hours and quenched with water (30.0 mL). The organic layer was washed with water (20.0 mL) and brine (20.0 mL), dried over magnesium sulphate, filtered off and concentrated under vacuum. The residue was adsorbed on silica gel and purified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (10CV*), 97/3 (5CV)] affording compound 2 as a colourless liquid (1.47 g, yield=58%).