tert-Butyl hydroperoxide → HCID 17862496, compound

Participants

Reaction Steps

According to a similar procedure to that described in Example 4-(5), 7-fluoro-1(3H)-isobenzofuranone (described in Tetrahedron, 54, 7485 (1998); 1.67 g, 11 mmol) was reacted with an aqueous solution of sodium hydroxide (1.008N; 10.9 ml, 11 mmol), 4-methoxybenzyl chloride (1.57 g, 10 mmol), tetrazole (1.40 g, 20 mmol), bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219 (1989); 3.1 g, 12.6 mmol), and tert-butyl hydroperoxide (80% di-tert-butyl peroxide solution; Merck; 2.7 g, 24 mmol), and the reaction mixture was worked up to afford, after extraction, an oily residue. The oily residue was subjected to chromatography on a silica gel (100 g) column (eluent; ethyl acetate:hexane=2:3) to afford a mixture of a solid and an oily material. The mixture was washed with a mixed solvent of ethyl acetate and hexane, the washings were concentrated under reduced pressure to give a residue. The residue was subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=1:4˜1:2) to afford the title compound (1.08 g, 24% yield) as a colorless oil.

Provenance & Evidence