Toluene → 2-(4-methyl-1H-1,2,3-triazol-1-yl)acetic acid

HRID 1888180Notes

Reaction equation

HRID 1888180 reaction equation
[N:1]([CH2:4][C:5]([O:7]CC)=[O:6])=[N+:2]=[N-:3].[C:10]1(C)[CH:15]=CC=C[CH:11]=1>>[CH3:15][C:10]1[N:3]=[N:2][N:1]([CH2:4][C:5]([OH:7])=[O:6])[CH:11]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 69480Acetic acid, azido-, ethyl ester

Product 1

HCID 185244432-(4-methyl-1H-1,2,3-triazol-1-yl)acetic acidYield 18%

Conditions

Temperature
120 °C

Procedure

To a solution of 2.0 g (18 mmol) of 1-(trimethylsilyl)-1-proyne in toluene (20 mL) was added 2.3 g (18 mmol) of ethyl azido-acetate. The reaction mixture was heated at 120° C. overnight then cooled to ambient temperature. All volatiles were removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with a 5-25% acetone in hexanes gradient to yield the title compound as a colorless oil (0.77 g, 18%). 1HNMR (500 MHz, CDCl3): δ 5.01 (s, 2H), 4.2 (m, 2H), 2.25 (s, 3H), 1.22 (m, 3H), 0.295 (s, 9H).

Workup

  1. temperaturethen cooled to ambient temperature
  2. customAll volatiles were removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel eluting with a 5-25% acetone in hexanes gradient

Sources & evidence

ORD record
ord-37850cffc58f43d19ee4e6b7bcae62e3
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

Loading…