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

反応式

[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

参加物

反応物 2

HCID 1140Toluene

HCID 69480Acetic acid, azido-, ethyl ester

生成物 1

HCID 185244434-Methyl-1H-1,2,3-triazole-1-acetic acid収率 18%

反応条件

温度: 120 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード: ord-37850cffc58f43d19ee4e6b7bcae62e3
出典データセット: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08501786B2

反応ノート

読み込み中…

参加物