반응 #73706

반응 방정식

H2SO4

29

1-(3-Bromo-2-hydroxy-5-methylphenyl)ethanone

Si(OEt)4

2,6-diisopropylaniline

→

yellowish solid

수율 82.0%

2-Bromo-6-[(1E)-N-(2,6-diisopropylphenyl)ethanimidoyl]-4-methylphenol

수율 82.0%

용매

반응 조건

후처리

1. 1
   workup.DISTILLATIONthe formed ethanol was slowly distilled off
2. 2
   workup.ADDITIONLater, 300 mL of cold water was added
3. 3
   추출the product was extracted with 2×100 mL of diethyl ether
4. 4
   추출The combined extract
5. 5
   건조was dried over K2CO3
6. 6
   기타evaporated to dryness
7. 7
   기타The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent
8. 8
   세척The isolated product was additionally washed with 3×30 mL hexanes
9. 9
   기타dried in vacuum

실험 절차

In a 50 mL Claisens flask under argon atmosphere, a mixture of 10.6 g (46.3 mmol) of 29, 20.2 g (97.2 mmol) of Si(OEt)4, and 9.03 g (50.9 mmol) of 2,6-diisopropylaniline was heated to 170° C., and then 0.37 mL of 96% H2SO4 was added. This mixture was stirred for 5 hr, and the formed ethanol was slowly distilled off. Later, 300 mL of cold water was added, and the product was extracted with 2×100 mL of diethyl ether. The combined extract was dried over K2CO3 and then evaporated to dryness. The product was isolated by flash-chromatography on silica gel 60 (40-63 um, eluent: hexanes and then hexanes-diethyl ether, 100:1, vol.). The isolated product was additionally washed with 3×30 mL hexanes and dried in vacuum. This procedure gave 14.7 g (82%) of yellowish solid.

출처