3-Cyanophenol → Ethyl[4-(3-Hydroxyphenyl)-1H-1,2,3-triazol-1-yl]acetate

HRID 82312

反応式

HRID 82312 の反応式
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+:2]=[N-:3].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#N.O=[C:20]1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][N:1]1[CH:20]=[C:14]([C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([OH:10])[CH:12]=2)[N:3]=[N:2]1)[CH3:9]

参加物

7

反応物 3

HCID 133943-CyanophenolHCID 69480Acetic acid, azido-, ethyl esterHCID 23667548Sodium Ascorbate

生成物 1

HCID 70847799Ethyl[4-(3-Hydroxyphenyl)-1H-1,2,3-triazol-1-yl]acetate

試薬・触媒・溶媒 3

HCID 24462Copper Sulfate触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

Ethyl azidoacetate (14.9 g, 115 mmol) was dissolved in tert-butanol (200 mL), and 95% 3-hydroxybenzonitrile (13.7 g, 110 mmol) was added. A solution of sodium ascorbate (2.18 g, 11 mmol) in water (100 mL) was added, followed by a 0.3 M solution of copper sulfate under argon. The mixture was stirred at room temperature for 12 hours. The solution was evaporated to dryness in vacuo, the residue was dissolved in EtOAc (100 mL), dried (MgSO4), filtered, evaporated in vacuo to give the title compound as brown crystals in ˜100% (27.7 g) yield.

後処理

  1. customThe solution was evaporated to dryness in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-6ebff5c06872415e8a04b5610978f174
出典データセット
uspto-grants-2014_09
特許番号
US08846698B2

関連ノート

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