Triphenylphosphine → HCID 86594117, compound

Participants

Reaction Steps

To a THF (1 mL) solution of compound from Example 21D (150 mg, 0.52 mmol), methyl 2,6-dihydroxybenzoate (336 mg, 2.0 mmol), and PPh3 (210 mg, 0.8 mmol) was added DEAD (140 mg, 0.8 mmol) at 0° C. Insoluble salt (phenolate/PPh3) formed quickly. The mixture was warmed to ambient temperature and dichloromethane (3 mL) was added, but the salt remained insoluble in this solvent system. A drop of water was added after 2 hours to decompose the salt, upon which the slurry turned into a homogeneous solution. The mixture was purified by flash column chromatography (30% ethyl acetate in hexanes) to provide the titled compound (130 mg, 40%).

Provenance & Evidence