[CH:1](=[N:5][OH:6])[CH:2]([CH3:4])[CH3:3].[CH2:7]([Cl:10])[C:8]#[CH:9].CCN(CC)CC.Cl([O-])=O.[Na+]>C(Cl)Cl>[Cl:10][CH2:7][C:8]1[O:6][N:5]=[C:1]([CH:2]([CH3:4])[CH3:3])[CH:9]=1To a stirring solution of 1.0 g (11.5 mmol) of isobutyraldehyde oxime, 0.9 g (12.1 mmol) of propargyl chloride, and 0.7 mL (5.02 mmol) of Et3N in 30 mL of CH2Cl2 at 0° C. was added 125 mL of sodium chlorite solution (>4% chlorine). The ice bath was removed and stirring was continued with warming to r.t. After 1.5 h, CH2Cl2 was added, and the organic layer was washed with 20 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided 1.14 g of 5-(chloromethyl)-3-isopropylisoxazole as a pale yellow liquid in about 62% yield. (60%)
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