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Dimethylformamide → 1-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-5-[4-(t-butyl-dimethyl-silanyloxymethyl)-phenyl]-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

HRID 623667
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 623667
CN(C=O)C.[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]([N:28]=[N+:29]=[N-:30])=[CH:16][C:15]=1[CH:31]([CH3:33])[CH3:32])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:34][O:35][C:36](=[O:54])[C:37]#[C:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]([CH3:53])([CH3:52])[O:46][SiH2:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:41][CH:40]=1.CCOC(C)=O>O>[CH3:34][O:35][C:36]([C:37]1[N:30]=[N:29][N:28]([C:17]2[CH:16]=[C:15]([CH:31]([CH3:33])[CH3:32])[C:14]([O:13][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[CH:19][C:18]=2[O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:38]=1[C:39]1[CH:40]=[CH:41][C:42]([C:45]([CH3:53])([CH3:52])[O:46][SiH2:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[CH:43][CH:44]=1)=[O:54]
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Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 715342021,5-Bis-benzyloxy-2-isopropyl-4-azido-benzeneHCID 131735183[4-(Tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-propynoic acid methyl ester

Produkt 1

HCID 1317351821-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-5-[4-(t-butyl-dimethyl-silanyloxymethyl)-phenyl]-1H-[1,2,3]triazole-4-carboxylic acid methyl ester
Ausbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A DMF solution (2.5 ml) containing 1,5-bis-benzyloxy-2-isopropyl-4-azido-benzene (373 mg, 1 mmol) and [4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-propynoic acid methyl ester (277 mg, 0.91 mmol) was degassed at RT by means of three vacuum-nitrogen cycles. [Cp*RuCl]4 (49 mg, 0.045 mmol) was then added and other three cycles were done. The reaction was stirred at RT until completion (monitored by TLC). AcOEt and water were then added. After standard work-up, the crude reaction mixture was purified by column chromatography (PE/AcOEt:60/40) to get the desired adduct as an oil.

Aufarbeitung

  1. customwas degassed at RT by means of three vacuum-nitrogen cycles
  2. customAfter standard work-up, the crude reaction mixture
  3. customwas purified by column chromatography (PE/AcOEt:60/40)

Quellen und Nachweise

ORD-Eintrag
ord-ab6481b38d39423f800c56a8da45d841
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09302998B2

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