Potassium Carbonate → (S)-3-(2-Amino-3-nitrophenoxy)-1,2-epoxypropane

反応式

[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].[N+](C1C=C(S(O[CH2:25][C@H:26]2[O:28][CH2:27]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH2:25][C@H:26]1[O:28][CH2:27]1

参加物

実験手順

5 g (0.032 mol) of 2-amino-3-nitrophenol, 8 g (0.032 mol) of (S)-(+)-glycidyl 3-nitrobenzenesulfonate and 8.9 g of K2CO3 are mixed in 80 ml of acetone and the mixture is refluxed for 18 hours. Filtration is carried out, the solvent is evaporated under reduced pressure and the crude product is purified by flash chromatography, elution being carried out with a 7/3 cyclohexane/ethyl acetate mixture. The solid product obtained is triturated in ethyl ether and 5.67 g of the title product are obtained. M.p.: 107-109°. αD+28.1 (c=0.5%, MeOH).