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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
ノート
印刷プレビュー

反応式

HRID 623667 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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
収率 68%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ab6481b38d39423f800c56a8da45d841
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09302998B2

反応ノート

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