tert-Butyl hydroperoxide → 4-Methoxybenzyl 2-[[bis(allyloxy)phosphoryl]oxymethyl]-5-fluorobenzoate

Participants

Reaction Steps

According to a similar procedure to that described in Example 4-(5), 6-fluoro-1(3H)-isobenzofuranone (described in Tetrahedron, 44, 4591 (1988); 1.52 g, 10 mmol) was reacted with an aqueous solution of sodium hydroxide (1.008N; 10 ml, 10 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); 3.0 g, 12.2 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 residue was subjected to chromatography on a silica gel (90 g) column (ethyl acetate:hexane=1:4˜1:2) to give an oily mixture. The mixture was further subjected to chromatography on a silica gel (50 g) column (eluent; ethyl acetate:hexane=1:4˜1:2) to afford the title compound (1.22 g, 27% yield) as a colorless oil.

Provenance & Evidence