反应详情

A mixture of 4-tert-butyl-3-hydroxy-benzoic acid methyl ester (1.56 g, 7.49 mmol), 3-bromopropyl methyl ether (1.72 g, 11.2 mmol) and anhydrous K2CO3 (1.55 g, 11.2 mmol) in MeCN (30 mL) is refluxed overnight. After cooling, the mixture is filtered, the filtrate is diluted with CH2Cl2 and the organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 97:3) gives the title compound as colorless oil. MS: 281.1 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 6.22 min. 1H-NMR (CDCl3): δ 1.43 (s, 9H), 2.17 (m, 2H), 3.41 (s, 3H), 3.65 (m, 2H), 3.93 (s, 3H), 4.18 (m, 2H), 7.36 (dd, 1H), 7.96 (d, 1H), 7.60 (dd, 1H) ppm.

1. temperatureis refluxed overnight
2. temperatureAfter cooling
3. filtrationthe mixture is filtered
4. additionthe filtrate is diluted with CH2Cl2
5. washthe organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated
8. customPurification by flash chromatography on silica gel (hexane/AcOEt 97:3)