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

HRID 82312

반응식

HRID 82312 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24462Copper Sulfate촉매HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6ebff5c06872415e8a04b5610978f174
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846698B2

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