Ethyl Acetate → 1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 928413Notes

Reaction equation

HRID 928413 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].C(OCC)(=O)C>CCCCO.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:18]([O:17][C:13]([C:14]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:10]=[CH:9][C:8]([CH2:11][OH:12])=[CH:7][CH:6]=2)[CH:15]=1)=[O:16])[CH3:19]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 12182Ethyl propiolateHCID 23132430[4-(Azidomethyl)phenyl]methanolHCID 23667548Sodium Ascorbate

Product 1

HCID 580812161-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

A mixture of (4-Azidomethyl-phenyl)-methanol (4.12 g, 25 mmol), ethyl propiolate (2.54 mL, 25 mmol), copper(II) sulfate (798 mg, 5 mmol) and sodium ascorbate (4.95 g, 25 mmol) in 30 mL n-BuOH and 30 mL water was stirred at room temperature for 16 h. Ethyl acetate was added and the mixture was extracted with water. The organic layer was dried over MgSO4 and evaporated in vacuo to give the title compound which was used in the next step without further purification. LCMS (Method A) RtA=1.157; [M+H]+=467.0MS [M+H]+=262.0.

Workup

  1. extractionthe mixture was extracted with water
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-51d6f9ded2894dfcb18e2eeba0ce5ab0
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

Loading…