Allyl bromide → HCID 15018887、化合物

HRID 344587ノート

反応式

HRID 344587 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[CH:8]=[CH2:9].[OH:11][C:12]1[CH:13]=[C:14]([N:18]2[C:22](=[O:23])[C:21]3[CH2:24][CH2:25][CH2:26][CH2:27][C:20]=3[C:19]2=[O:28])[CH:15]=[CH:16][CH:17]=1>CC(C)=O>[CH2:7]([O:11][C:12]1[CH:13]=[C:14]([N:18]2[C:19](=[O:28])[C:20]3[CH2:27][CH2:26][CH2:25][CH2:24][C:21]=3[C:22]2=[O:23])[CH:15]=[CH:16][CH:17]=1)[CH:8]=[CH2:9]

参加物

5

反応物 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 127692364,5,6,7-Tetrahydro-2-(3-hydroxyphenyl)-1H-isoindole-1,3(2H)-dione

生成物 1

HCID 15018887HCID 15018887、化合物

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

3.0 g of powdered potassium carbonate, then 2.6 g of allyl bromide were added to a stirred suspension of 5.0 g of 1A in 25 mL of acetone. The mixture was refluxed for 1 hour, then stirred overnight at room temperature. The solvent was evaporated, water was added to the residue and the pH of the mixture was adjusted to 11 by addition of 10% aqueous sodium hydroxide. The resulting mixture was extracted with ethyl acetate, the extract was washed with brine and dried (Na2SO4), the solvent was evaporated and the residue was flash chromatographed on silica gel with a 1:9 v:v mixture of ethyl acetate and hexane as eluent to give N-(3-allyloxyphenyl)-3,4,5,6-tetrahydrophthalimide (1B), as yellow crystals, m.p.: 88°-90° C.

後処理

  1. temperatureThe mixture was refluxed for 1 hour
  2. customThe solvent was evaporated
  3. additionwater was added to the residue
  4. additionthe pH of the mixture was adjusted to 11 by addition of 10% aqueous sodium hydroxide
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washthe extract was washed with brine
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated
  9. customchromatographed on silica gel with a 1:9 v
  10. additionv mixture of ethyl acetate and hexane as eluent

出典と根拠

ORDレコード
ord-bf40aaf5dc07422ab7737d0c7c378cea
出典データセット
uspto-grants-1991_10
特許番号
US05053071

反応ノート

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