Benzyl Alcohol → Methyl 3-(benzyloxy)-4-nitrobenzoate

Participants

Reaction Steps

Methyl-3-hydroxy-4-nitrobenzoate Cmpd 1 (1.0 g, 1.0 eq) was dissolved in THF (6 mL) in a microwave vial. Benzyl alcohol (1.0 eq) and PPh3 (1.0 eq) were added to the vial. The reaction vial was put under nitrogen flow, and DIAD (1.0 eq) was added in the dark after stirring the reaction for 1.5 hours. The reaction was microwave irradiated at 100° C. for 6 min (Biotage Initiator™ Eight). The solution was concentrated, and purification of the resultant was performed on a SP1 flash chromatography system (Biotage™) starting with 6% EtOAc: 94% Hex to 60% EtOAc: 40% Hex. The recovered yellow solid was treated with MP-Carbonate resin (2 eq) in DCM and the mixture was shaken overnight at RT. The resin was filtered and multiply washed with DCM. The filtrate was concentrated under vacuum to give Cmpd 2 as a yellow solid (1.39 g, 94% yield).

Provenance & Evidence