Toluene → 4-Methyl-1H-1,2,3-triazole-1-acetic acid

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

Reactant 2

HCID 1140Toluene

HCID 69480Acetic acid, azido-, ethyl ester

Product 1

HCID 185244434-Methyl-1H-1,2,3-triazole-1-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

temperaturethen cooled to ambient temperature
customAll volatiles were removed under reduced pressure
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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501786B2

Reaction notes

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