Hydrochloric Acid → 2-(4-Chloro-2-ethynylphenyl)propanenitrile

反応式

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[C:4]([C:12]#[C:13][Si](C)(C)C)[CH:3]=1.[OH-].[Na+].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[C:4]([C:12]#[CH:13])[CH:3]=1

参加物

実験手順

To a solution of 2-(4-chloro-2-(2-(trimethylsilyl)ethynyl)phenyl)-propanenitrile (0.550 g, 2.1 mmol) in THF (25 mL) was added 5N NaOH (15 mL). After one hour, the reaction was complete as determined by LC-MS and TLC. The solution was acidified with 5N HCl until the pH was about 2. The solution was extracted with EtOAc (3×40 mL). The combined organic layers were washed with water (2×30 mL) and brine (2×30 mL), dried with MgSO4, and concentrated in vacuo. The resulting orange oil was purified using silica flash chromatography on the ISCO with 0-20% EtOAc/hexanes. MS m/e=190 (M+H)+.