反应详情

A mixture of methyl 3-hydroxy-4-methoxybenzoate (4.94 g, 26.6 mmol), 3-bromo-1-propanol (2.86 mL, 31.9 mmol) and anhydrous K2CO3 (5.51 g, 39.9 mmol) in MeCN (50 mL) is refluxed with stirring overnight, and after cooling is poured into ice/water. The aqueous layer is extracted with AcOEt, and the combined organics are washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 1:2) gives a solid residue which is stirred in a 9:1 mixture of hexane/AcOEt over 30 min. Filtration of the suspension and drying in vacuo gives the title compound as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.09. MS: 241.2 [M+H]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 2.86 min. 1H-NMR (CDCl3): δ 2.13 (m, 2H), 2.59 (m, 1H), 3.92 (s, 3H), 3.93 (s, 3H), 4.29 (m, 2H), 6.92 (m, 1H), 7.60 (s, 1H), 7.73 (m, 1H) ppm.

1. temperatureis refluxed
2. temperatureafter cooling
3. extractionThe aqueous layer is extracted with AcOEt
4. washthe combined organics are washed with brine
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customPurification by flash chromatography on silica gel (hexane/AcOEt 1:2)
8. customgives a solid residue which
9. filtrationFiltration of the suspension
10. customdrying in vacuo