反応 #521210

ord-8655af1fcd1c4c9a8078c341113f32f9

反応方程式

ON=C(Cl)c1ccccc1F
2-fluorobenzoylchloride oxime
CC#CC(=O)OC
methyl-2-butynoate
CCN(CC)CC
Et3N
COC(=O)c1c(-c2ccccc2F)noc1C
title compound
収率 58.0%
COC(=O)c1c(-c2ccccc2F)noc1C
4-Methoxycarbonyl-5-methyl-3-(2-fluorophenyl)isoxazole
収率 58.0%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    洗浄washed (H2O
  2. 2
    乾燥brine), dried (MgSO4)
  3. 3
    ろ過filtered
  4. 4
    濃縮concentrated

実験手順

To a solution (0° C., N2) of 2-fluorobenzoylchloride oxime (0.50 g, 2.9 mmol) and methyl-2-butynoate (0.57 g, 5.8 mmol) in Et2O (15 ml) was added a solution of Et3N (0.52 ml) in Et2O (2 ml) over a period of 1 h followed by warming to room temperature while stirring overnight (17 h). The reaction was diluted with Et2O, washed (H2O then brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/EtOAc gradient) gave the title compound (0.39 g, 58%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06670373B1uspto-grants-2003_12