tert-Butyl hydroperoxide → Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methoxybenzyl phosphate

Participants

Reaction Steps

According to a similar procedure to that described in Example 1-(10), 2-[(tert-butyldimethylsilyl)oxymethyl]-6-methoxybenzyl alcohol (1.13 g, 4.00 mmol) obtained from Example 21-(2), tetrazole (672.3 mg, 9.6 mmol), bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219 (1989); 1.37 g, 5.6 mmol), and tert-butyl hydroperoxide (80% di-tert-butyl peroxide solution; Merck; 0.9 g, 8 mmol) were reacted, and the reaction mixture was worked up to afford, after extraction, an oily residue. The residue was subjected to chromatography on a silica gel (60 g) column (eluent; ethyl acetate:hexane=1:6˜1:2) to give the title compound (1.07 g, 60% yield) as a colorless oil.

Provenance & Evidence