反応 #81605

反応方程式

ethyl 3-[3-bromo-5-[(4-fluorophenyl)hydroxymethyl]phenyl]-2-propenoate

acrylamide

tri-o-tolylphosphine

triethylamine

→

title compound

収率 59.4%

Ethyl 3-[3-(2-carbamoylethenyl)-5-[(4-fluorophenyl)-hydroxymethyl]phenyl]2-propenoate

収率 59.4%

溶媒

acetonitrile

dichloromethane

Water

反応条件

後処理

1. 1
   温度cooled
2. 2
   温度the mixture was warmed
3. 3
   workup.ADDITIONto disperse the solid residue
4. 4
   温度The mixture was cooled
5. 5
   ろ過filtered
6. 6
   workup.DISSOLUTIONthe solid was dissolved in hot isopropanol (500 ml)
7. 7
   ろ過The solution was filtered hot
8. 8
   濃縮the filtrate was concentrated until crystallisation
9. 9
   workup.ADDITIONAn equal volume of ether was added
10. 10
    温度to cool
11. 11
    ろ過The solid was filtered off
12. 12
    その他dried

実験手順

A mixture of ethyl 3-[3-bromo-5-[(4-fluorophenyl)hydroxymethyl]phenyl]-2-propenoate (9.50 g), acrylamide (2.67 g), palladium(II) acetate (0.306 g), tri-o-tolylphosphine (0.763 g) and triethylamine (3.80 g) in acetonitrile (10 ml) was heated to 100° C. for 4 hours under an atmosphere of nitrogen and then cooled. Water (150 ml) and dichloromethane (150 ml) was added and the mixture was warmed with stirring to disperse the solid residue. The mixture was cooled and filtered, and the solid was dissolved in hot isopropanol (500 ml). The solution was filtered hot using a filter aid, and the filtrate was concentrated until crystallisation commenced. An equal volume of ether was added and the mixture was allowed to cool. The solid was filtered off and dried to give the title compound (5.50 g), m.p. 197°-199° C. Found: C,68.55; H,5.17; N,4.01. C21H20FNO4 requires C,68.28; H,5.46; N,3.79%.

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