4-Methoxybenzyl alcohol → HCID 89463489, compound

Participants

Reaction Steps

To a solution of dimethyl 1H-pyrazole-3,4-dicarboxylate (2.5 g, 13.6 mmol) in THF (100 mL) was added 4-methoxybenzyl alcohol (1.78 mL, 14.2 mmol) and triphenylphosphine 3.74 g, 14.2 mmol) followed by dropwise addition of DIAD (2.8 mL, 14.2 mmol) and the mixture was stirred at ambient temperature under nitrogen atmosphere for 3 h. The mixture was diluted with EtOAc and washed with saturated sodium bicarbonate/water. The organic phase was dried over sodium sulfate, concentrated and purified on silica using EtOAc/hexanes 0-50% to provide the title compound (1.4 g, 32%) and isomer dimethyl 1{{4-(methyloxy)phenyl]methyl}-1H-pyrazole-3,4-dicarboxylate (1.3 g, 29%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.98 (s, 1H), 7.18 (d, 2H), 6.9 (d, 2H), 5.4 (s, 2H), 3.92 (s, 3H), 3.89 (s, 3H), 3.87 (s, 3H); ES-LCMS: 305.28 (M+1).

Provenance & Evidence