2-Methoxyphenethyl alcohol → 3-(5-(2-methoxyphenethoxy)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzonitrile

Participants

Reaction Steps

A suspension of 130 (200 mg, 0.790 mmol) and PS-PPh2 (2.15 mmol/g, 0.522 g, 1.5 eq, polymer supported triphenylphosphine) in THF (7 mL) under a nitrogen atmosphere was stirred for 10 minutes. DIAD (0.154 mL, 0.790 mmol) was added and after 1 hour of stirring at room temperature 2-methoxy-phenethyl alcohol (0.112 mL, 0.790 mmol) was added and the suspension was stirred for 48 h. The reaction mixture was filtered and the resin washed with DCM, the filtrate was concentrated and the residue purified by silica gel chromatography (Biotage 25M, 5-20% ethyl acetate in hexanes) to give 131 (86 mg, 0.222 mmol, 28.1% yield) as white solid. LRMS(ESI): (calc.) 387.4 (found) 388.1 (MH)+, 410.0 (MNa)+.

Provenance & Evidence