Catecholborane → trans-3-Methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid

HRID 54279

反応式

HRID 54279 の反応式
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)([CH3:5])[C:3]#[CH:4].[O:16]1C2C=CC=CC=2[O:18][BH:17]1>>[CH3:5][C:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:14])([F:13])[F:15])=[CH:8][CH:7]=1)([CH3:1])/[CH:3]=[CH:4]/[B:17]([OH:18])[OH:16]

参加物

3

反応物 2

HCID 67506CatecholboraneHCID 153325731-(2-Methylbut-3-yn-2-yl)-4-(trifluoromethyl)benzene

生成物 1

HCID 21468004trans-3-Methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid収率 89.1%

反応条件

温度
70 °C

実験手順

Under a nitrogen atmosphere, a stirred mixture of 25.2 grams (0.12 mole) of 3-methyl-3-(4-trifluoromethylphenyl)-1-butyne and 12.7 mL (0.12 mole) of 1,3,2-benzodioxaborole was warmed to 70° C. where it stirred for six hours. The reaction mixture was then cooled and poured slowly into 500 mL of ice-water while flushing with nitrogen. The mixture was then allowed to warm to ambient temperature where it stirred for about 18 hours. The mixture was cooled in an ice-bath, and the resultant solid was collected by filtration. The solid was washed with water and then dissolved in diethyl ether. The solution was washed with 100 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and concentrated under reduced pressure to a residual solid. The solid was added under vacuum without heat, yielding 27.6 grams of trans-3-methyl-3-(4-trifluoromethylphenyl)-1-butenylboronic acid.

後処理

  1. temperatureThe reaction mixture was then cooled
  2. customwhile flushing with nitrogen
  3. temperatureto warm to ambient temperature where it
  4. stirringstirred for about 18 hours
  5. temperatureThe mixture was cooled in an ice-bath
  6. filtrationthe resultant solid was collected by filtration
  7. washThe solid was washed with water
  8. dissolutiondissolved in diethyl ether
  9. washThe solution was washed with 100 mL of an aqueous solution saturated with sodium chloride
  10. dry with materialThe organic layer was dried with magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure to a residual solid
  13. additionThe solid was added under vacuum
  14. temperaturewithout heat

出典と根拠

ORDレコード
ord-6a7c54c4006142cf901db79431090812
出典データセット
uspto-grants-1997_04
特許番号
US05622954

関連ノート

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