N-Fluorobenzenesulfonimide → HCID 59739630, compound

Participants

Reaction Steps

5,5-Dimethyl-3-(2-trifluoromethoxy-phenylmethanesulfonyl)-4,5-dihydroisoxazole (0.2 g, 0.59 mmol) was dissolved in acetonitrile (5 ml) and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (Verkade's base) (0.44 ml, 1.24 mmol) was added dropwise at room temperature. After 5 minutes N-fluorobenzene-sulfonimide (NFSI) (393 mg, 1.24 mmol) was added in one portion. After 10 minutes the reaction was quenched by addition of water (10 ml). The mixture was acidified by addition of aqueous hydrochloric acid (2M) and extracted several times with ethyl acetate (3×10 ml). The combined organic phases were washed with saturated aqueous sodium hydrogencarbonate solution and with water, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (Compound No. 1.68 of Table 27) as colourless oil (145 mg, 69% yield).

Provenance & Evidence