Hydrochloric Acid → HCID 83815810, compound

Participants

Reaction Steps

To a solution of the phenol of Example 150 Step 1 (5.0 g, 36.7 mmol) in 200 mL CH3CN, was added MgCl2 (5.25 g, 55.1 mmol), TEA (13.9 g, 19.2 mL, 137.6 mmol), and (CHO)N (8.3 g, 280 mmol). The reaction was heated at reflux for 3 h. After cooling, the reaction was diluted with EtOAc (500 mL) and acidified with aqueous 2N HCl until the reaction was pH 4. The reaction was diluted with 300 mL H2O. The organic layer was washed with H2O, with brine, dried over MgSO4, and concentrated. The residue was purified by flash chromatography (on SiO2, hexane/EtOAc=94/6) to give 3.2 g (53%) of the desired product as a clear oil.

Provenance & Evidence