Triphenylphosphine → 4-[((1S)-2-(benzyloxy)-1-{[(triisopropylsilyl)oxy]methyl}ethyl)oxy]-4'-(trifluoromethoxy)-1,1'-biphenyl

Participants

Reaction Conditions

Reaction Steps

1,1′-Diisopropyl azodicarboxylate (7.70 mL, 0.039 mol) was added dropwise at 5° C. to a solution of the alcohol 79 (12.40 g, 0.037 mol), 4′-(trifluoromethoxy)[1,1′-biphenyl]-4-ol (reported by Edsall et al., 2003, via Suzuki coupling of 4-bromophenol and boronic acid 44) (8.29 g, 0.033 mol) and triphenylphosphine (10.26 g, 0.039 mol) in anhydrous benzene (25 mL) and the solution was stirred at 20° C. for 18 h. The product was adsorbed directly onto silica by concentration under reduced pressure, and chromatography on silica gel, eluting with EtOAc/petroleum ether (1:19), gave 4-[((1S)-2-(benzyloxy)-1-{[(triisopropylsilyl)oxy]methyl}ethyl)oxy]-4′-(trifluoromethoxy)-1,1′-biphenyl (80) (14.30 g, 69%) as a colourless oil: [α]19 +5.9° (c, 6.95, CHCl3); 1H NMR (CDCl3) δ 7.72 (d, J=8.8 Hz, 2H), 7.58 (d, J=8.8 Hz, 2H), 7.40 (d, J=8.8 Hz, 2H), 7.35-7.24 (m, 5H), 7.06 (d, J=8.8 Hz, 2H), 4.64-4.57 (m, 1H), 4.52 (s, 2H), 3.98-3.87 (m, 2H), 3.76-3.65 (m, 2H), 1.08-0.98 (m, 21H). APCI MS m/z 576 [M+H]+.

Provenance & Evidence