反应详情

A mixture of 4-(1-imidazolyl)benzaldehyde (5.08 g, 29.5 mmol) and methyl(methylthio)methylsulfoxide (2.57 g, 21 mmol) in THF (5 mL) was treated with a 40% methanolic solution of TRITON® B (3 mL). The reaction mixture was refluxed for 4 hours, additional methyl(methylthio)methylsulfoxide (1.09 g, 8.5 mmol) was added and the reaction mixture was refluxed for an additional 2 hours. The reaction mixture was cooled to room temperature, CH2Cl2 was added and the organic layer was washed with water, then brine and then was dried over MgSO4, filtered and stripped. The residue was taken up in ethanolic HCl (180 mL) and refluxed for 16 hours. The reaction mixture was cooled, the ethanol was stripped and the residue was treated with water (200 mL) and extracted with ethyl acetate (250 mL). The aqueous layer was treated with dilute NH4OH and extracted with ethyl acetate (2×) and then the organic layer was washed with brine, dried over MgSO4, filtered and stripped to afford crude product. The crude product was taken up in ethyl acetate, shaken with 25% sodium bisulfite and then brine. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried over MgSO4, filtered and stripped to afford 1.93 g of ethyl 4-(1-imidazolyl)phenylacetate.

1. temperatureThe reaction mixture was refluxed for 4 hours
2. temperaturethe reaction mixture was refluxed for an additional 2 hours
3. washthe organic layer was washed with water
4. dry with materialbrine and then was dried over MgSO4
5. filtrationfiltered
6. temperaturerefluxed for 16 hours
7. temperatureThe reaction mixture was cooled
8. additionthe residue was treated with water (200 mL)
9. extractionextracted with ethyl acetate (250 mL)
10. additionThe aqueous layer was treated with dilute NH4OH
11. extractionextracted with ethyl acetate (2×)
12. washthe organic layer was washed with brine
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. customto afford crude product
16. extractionThe aqueous layer was extracted with ethyl acetate
17. dry with materialthe combined organic layers were dried over MgSO4
18. filtrationfiltered