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Potassium Carbonate → 3-[4-((E)-2-{4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenyl}-vinyl)-3,5-dimethyl-phenyl]-2,2-dimethyl-propionic acid methyl ester

HRID 1360804
ノート
印刷プレビュー

反応式

HRID 1360804 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[N:12][N:13]=2)=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:43][O:44][C:45](=[O:60])[C:46]([CH3:59])([CH3:58])[CH2:47][C:48]1[CH:53]=[C:52]([CH3:54])[C:51]([CH:55]=O)=[C:50]([CH3:57])[CH:49]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:43][O:44][C:45](=[O:60])[C:46]([CH3:58])([CH3:59])[CH2:47][C:48]1[CH:53]=[C:52]([CH3:54])[C:51](/[CH:55]=[CH:2]/[C:3]2[CH:8]=[CH:7][C:6]([C:9]3[O:10][C:11]([C:14]4[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=4)=[N:12][N:13]=3)=[CH:5][C:4]=2[N+:21]([O-:23])=[O:22])=[C:50]([CH3:57])[CH:49]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 669664172-(4-Bromomethyl-3-nitro-phenyl)-5-(4-chloro-phenyl)-[1,3,4]oxadiazoleHCID 86632822Methyl 3-(4-formyl-3,5-dimethylphenyl)-2,2-dimethylpropanoate2 回

生成物 1

HCID 669664153-[4-((E)-2-{4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenyl}-vinyl)-3,5-dimethyl-phenyl]-2,2-dimethyl-propionic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Combine 2-(4-bromomethyl-3-nitro-phenyl)-5-(4-chloro-phenyl)-[1,3,4]oxadiazole (894 mg, 2.27 mmol) and PPh3 (656 mg, 2.50 mmol) in DMF (13 mL) and heat to 95° C. under N2 for 4.5 h. Add 3-(4-formyl-3,5-dimethyl-phenyl)-2,2-dimethyl-propionic acid methyl ester (intermediate A in Example 1-62, 675 mg, 2.72 mmol) and K2CO3 (627 mg, 4.54 mmol), continue heating at 95° C. for 6.5 h. Allow the reaction to cool to room temperature. Dilute the cooled reaction with EtOAc (150 mL) and extract with water (50 mL). Dry the organic layer over Na2SO4 and evaporate the solvent. Purify the resulting oil by silica gel chromatography (10-45% EtOAc/HEP) to afford a yellow solid: (M+H)+ 546.1.

後処理

  1. customthe reaction
  2. additionDilute
  3. extractionextract with water (50 mL)
  4. dry with materialDry the organic layer over Na2SO4
  5. customevaporate the solvent
  6. customPurify the resulting oil by silica gel chromatography (10-45% EtOAc/HEP)
  7. customto afford a yellow solid

出典と根拠

ORDレコード
ord-4b5e979194144037b60bef526258fa0d
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879850B2

反応ノート

読み込み中…

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