반응 #9722

반응 방정식

ethyl 2-bromo-2-methylpropanoate

1-(4-hydroxy-3-methylphenyl)ethanone

cesium carbonate

ethyl 2-bromo-2-methylpropanoate

→

title compound

ethyl 2-(4-acetyl-2-methylphenoxy)-2-methylpropanoate

용매

ethyl acetate

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture stirred for 25 hours
2. 2
   workup.STIRRINGthe mixture stirred for a further 16 hours
3. 3
   여과The mixture was filtered
4. 4
   농축the filtrate concentrated
5. 5
   기타to give an orange oil
6. 6
   세척the solution washed thrice with 1M sodium hydroxide and brine
7. 7
   기타The organic layer was separated
8. 8
   건조dried over sodium sulfate
9. 9
   여과filtered
10. 10
    농축the filtrate concentrated
11. 11
    기타the resulting oil was purified by Biotage® chromatography
12. 12
    세척eluting with cyclohexane:ethyl acetate (9:1)

실험 절차

A suspension of 1-(4-hydroxy-3-methylphenyl)ethanone (20.1 g) in acetonitrile (200 ml) was added to a suspension of cesium carbonate (86.6 g) in acetonitrile (400 ml) and the mixture stirred under nitrogen at room temperature for 2 minutes. ethyl 2-bromo-2-methylpropanoate (33 g) was added and the mixture stirred for 25 hours, further ethyl 2-bromo-2-methylpropanoate (33 g) was added and the mixture stirred for a further 16 hours. The mixture was filtered and the filtrate concentrated to give an orange oil, the oil was dissolved in ethyl acetate and the solution washed thrice with 1M sodium hydroxide and brine. The organic layer was separated, dried over sodium sulfate, filtered and the filtrate concentrated; the resulting oil was purified by Biotage® chromatography eluting with cyclohexane:ethyl acetate (9:1) to give the title compound as a clear oil.

출처