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

Participants

Reaction Steps

According to a similar procedure to that described in Example 1-(10), 2-[(tert-butyldimethylsilyl)oxymethyl]-6-chlorobenzyl alcohol (3.66 g, 12.8 mmol) obtained from Example 27-(1), tetrazole (2.23 g, 31.9 mmol), bis(allyloxy)(diisopropylamino)phosphine (described in Tetrahedron Lett., 30, 4219 (1989); 3.91 g, 16.0 mmol), and tert-butyl hydroperoxide (ca. 80% di-tert-butyl peroxide solution; Merck; 1.8 g, ca. 16 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 (200 g) column (eluent; ethyl acetate:hexane=1:5˜2:3) to afford the title compound (4.52 g, 79% yield) as a colorless oil.

Provenance & Evidence