Water → 3-(1-Chloroethyl)-5-t-butylisoxazole

Reaction equation

[C:1]([C:5]1[O:9][N:8]=[C:7]([CH:10](O)[CH3:11])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([Cl:22])(=O)=O)=CC=1.O>N1C=CC=CC=1>[Cl:22][CH:10]([C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[O:9][N:8]=1)[CH3:11]

Participants

Procedure

1.18 g of 1-(5-t-butyl-isoxazol-3-yl)ethanol was dissolved in 2 ml of pyridine, and 1.36 of 4-toluenesulfonyl chloride was then added under ice-cooling. The mixture was stirred for 5 hours under ice-cooling. After water was added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.60 g of 3-(1-chloroethyl)-5-t-butylisoxazole.