反应详情

Methyl 3-hydroxy-4-methoxybenzoate and 2-(3-chlorophenyl)-ethanol were reacted in analogy to step 1 of example 1. The obtained 3-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester (300 mg, 0.935 mmol), N-chloro-succinimide (381 mg, 2.81 mmol), and zirconium tetrachloride (129 mg, 0.57 mmol) were suspended in DCM (4 ml) and the mixture was stirred under reflux for 5 h until the starting material was used up. The mixture was partitioned between EA and a saturated aqueous sodium hydrogencarbonate solution, the aqueous phase extracted with EA, and the combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica chromatography (HEP/EA gradient) to give 118 mg of the title compound.

1. temperatureunder reflux for 5 h until the starting material
2. customThe mixture was partitioned between EA
3. extractiona saturated aqueous sodium hydrogencarbonate solution, the aqueous phase extracted with EA
4. dry with materialthe combined organic extracts were dried over sodium sulfate
5. filtrationfiltered
6. customevaporated to dryness
7. customThe residue was purified by silica chromatography (HEP/EA gradient)