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Ammonium formate → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

HRID 2383369
ノート
印刷プレビュー

反応式

HRID 2383369 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:6][CH:5]=1.C([O-])=O.[NH4+]>C(O)C.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]2=[O:21])=[CH:8][CH:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 2723923Ammonium formate2 回HCID 670291452-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

生成物 1

HCID 591459612-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

試薬・触媒・溶媒 3

HCID 9942167Palladium hydroxide触媒2 回HCID 702Ethanol溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 2-{2-[4-(2-Hydroxy-ethyl)-phenyl]-vinyl}-isoindole-1,3-dione (Preparation 9, 10 g) in ethanol and ethyl acetate (350 mL each) was added 30% palladium hydroxide on carbon (1.44 g) followed by ammonium formate (21.5 g). The reaction was heated to 80° C. for 4 hours. Additional palladium hydroxide on carbon (1.44 g) and ammonium formate (21.5 g) were added and the reaction was stirred at 80° C. for 18 hours. The reaction was cooled, filtered through a pad of Arbocel® and rinsed with methanol. The solvent was removed under reduced pressure and the resulting white solid was partitioned between dichloromethane (200 ml) and water (100 ml). The aqueous layer was separated and extracted with further dichloromethane (2×50 mL). The combined organic layers were dried (sodium sulphate) and the solvent removed in vacuo to give the title compound as an off-white solid, 9.11 g.

後処理

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through a pad of Arbocel®
  3. washrinsed with methanol
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting white solid was partitioned between dichloromethane (200 ml) and water (100 ml)
  6. customThe aqueous layer was separated
  7. extractionextracted with further dichloromethane (2×50 mL)
  8. dry with materialThe combined organic layers were dried (sodium sulphate)
  9. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-c06ddca49df84140a8c9b8ce0816efed
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263623B2

反応ノート

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