Triphenylphosphine → 2-(3-{[tert-butyl(dimethyl)silyl]oxy}-1-methylpropyl)-5-(3-chlorophenyl)-2H-tetrazole

Participants

Reaction Conditions

Reaction Steps

To triphenylphosphine (2.6 g, 10 mmol) in THF (50 mL) at 0° C. under argon, DEAD (1.6 mL, 10 mmol) added during 5 minutes. After stirring for 40 minutes at 0° C. 5-(3-chlorophenyl)-2H-tetrazole (0.90 g, 5 mmol) followed by a solution of 4-{[tert-butyl(dimethyl)silyl]oxy}butan-2-ol (1.53 g, 7.5 mmol) (Tett. 2003, 59, 4739-4748) in THF (5 mL) was added. Stirring at 0° C. for 10 minutes was followed by 21 h at r.t. The mixture was concentrated and purified by flash column chromatography (SiO2, Heptane-EtOAc 7:1) to give 1.8 g (98%) of the title compound.

Provenance & Evidence