Iodine → HCID 22131264, compound

Participants

Reaction Steps

A suspension of magnesium powder (409 mg, 16.8 mmol) in THF (10 ml) containing a few crystals of iodine was heated whilst a solution of 1-bromo-2,4-dimethoxybenzene (3.65 g, 16.8 mmol) in THF (20 ml) was added dropwise over 20 minutes. After completion of the addition, the mixture was refluxed for 1.25 hours and then allowed to cool to room temperature. The Grignard solution was transferred via syringe to a solution of 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (J. Org. Chem., 1978, 43, 1372, 2.50 g, 12.9 mmol) in THF (10 ml) at room temperature and the mixture was stirred at room temperature for 42 hours. Saturated ammonium chloride solution was added and the product was extracted into diethyl ether. The extracts were dried (K2CO3) and concentrated. Purification by column chromatography on silica gel (elution with 40-60% ethyl acetate in iso-hexane) gave the title compound as a viscous oil. Yield 4.029 g (84%).

Provenance & Evidence