Succinimide → 7-Nitroisochroman

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[2-(hydroxymethyl)-4-nitrophenyl]ethanol (Step 1, 1.65 g, 8.37 mmol), succinimide (829 mg, 8.37 mmol) and triphenylphosphine (2.46 g, 9.37 mmol) in dry THF at 0° C. under N2 is treated with diethyl azodicarboxylate (1.50 mL, 9.54 mmol) dropwise over 5 mins, and the resulting mixture is stirred at 0° C. for 4 hrs and then concentrated under reduced pressure. The residue is chromatographed on a Flash 40M silica gel (90 g, 32-63 μm) cartridge, eluting with EtOAc/heptane (10/90), and those fractions with an Rf=0.60 by TLC (EtOAc/hexane, 50/50) are pooled and concentrated to give 995 mg (66%) of the title compound as a white solid, mp 96-98° C.

Provenance & Evidence