تفاعل #9722

معادلة التفاعل

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

المذيبات

ethyl acetate

acetonitrile

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture stirred for 25 hours
2. 2
   workup.STIRRINGthe mixture stirred for a further 16 hours
3. 3
   ترشيحThe mixture was filtered
4. 4
   تركيزthe filtrate concentrated
5. 5
   أخرىto give an orange oil
6. 6
   غسيلthe solution washed thrice with 1M sodium hydroxide and brine
7. 7
   أخرىThe organic layer was separated
8. 8
   تجفيفdried over sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزthe filtrate concentrated
11. 11
    أخرىthe resulting oil was purified by Biotage® chromatography
12. 12
    غسيلeluting with cyclohexane:ethyl acetate (9:1)

الإجراء التجريبي

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.

المصدر