tert-Butyl hydroperoxide → Diallyl 2-[(tert-butyldimethylsilyl)oxymethyl]-6-chlorobenzyl phosphate
反応式
[Si:1]([O:8][CH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:11]=1[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=NN=N1.[CH2:24]([O:27][P:28]([O:36][CH2:37][CH:38]=[CH2:39])N(C(C)C)C(C)C)[CH:25]=[CH2:26].C([O:44]O)(C)(C)C>>[P:28]([O:13][CH2:12][C:11]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:10]=1[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])([O:27][CH2:24][CH:25]=[CH2:26])([O:36][CH2:37][CH:38]=[CH2:39])=[O:44]参加物
5
実験手順
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.