Acetonitrile → 2-(3-Cyano-phenoxy)-2-methyl-propionic acid ethyl ester

反応式

[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].C([CH2:12][C:13](Br)([CH3:17])[C:14]([O-:16])=[O:15])C.C(=O)([O-])[O-].[K+].[K+].[C:25](#N)[CH3:26]>>[CH2:25]([O:16][C:14](=[O:15])[C:13]([O:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=1)([CH3:12])[CH3:17])[CH3:26]

参加物

反応物 4

HCID 6342Acetonitrile

HCID 11430Potassium Carbonate

HCID 133943-Cyanophenol

HCID 22490247Ethyl-bromoisobutyrate

生成物 1

HCID 582440942-(3-Cyano-phenoxy)-2-methyl-propionic acid ethyl ester

反応条件

温度: 80 °C

実験手順

5.0 g (42.0 mmol) of 3-hydroxybenzonitrile and 16.25 ml=21.29 g (109 mmol) of ethyl-bromoisobutyrate were dissolved in 70 ml acetonitrile; then, 17.40 g (126 mmol) of potassium carbonate were added and the reaction mixture stirred for 16 hours at 80° C. (reflux). It was then cooled down to ambient temperature and the solvent was evaporated. The residue was partitioned between water and ether and extracted twice with ether; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, heptane/AcOEt) to finally give 9.10 g of the title compound as colorless oil.