Tetrabutylammonium Fluoride → HCID 136395592, compound

Participants

Reaction Steps

To a stirring solution consisting of (1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-methanol (compound E, Example 1) (18.2 g) in tetrahydrofuran (200 mL) at room temperature under a nitrogen atmosphere is added a 1.0 M solution consisting of tetrabutylammonium fluoride in tetrahydrofuran (45.3 mL.) The reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (1:1 v/v) afforded 12 g of a residue. The residue is dissolved in warm methanol. Addition of hexanes caused precipitation of a solid that is collected by filtration (11 g.) The solid is redissolved in warm methanol and again is precipitated with hexanes to afford a new crop of solid product (8.1 g); melting point 210-211° C.; MS (APCI+) m/z 308 (MH+.)

Provenance & Evidence