Phenol → HCID 57894208、化合物

HRID 1822294ノート

反応式

HRID 1822294 の反応式
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=3Br)[CH:15]=2)=[CH:9][C:8]=1[CH3:33])[CH3:2].[C:35]1([OH:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>CN1CCCC1=O.[Cu]Cl>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[C:16]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][C:23]=3[O:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH:17]=[C:18]([CH3:20])[CH:19]=2)=[CH:9][C:8]=1[CH3:33])[CH3:2]

参加物

7

反応物 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 57894173HCID 57894173、化合物

生成物 1

HCID 57894208HCID 57894208、化合物収率 54.6%

試薬・触媒・溶媒 2

HCID 62652Cuprous chloride触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

A mixture of 3-{4-[3-(2-bromo-4-trifluoromethyl-phenoxy)-5-methyl-phenoxy]-2-methyl-phenyl}-propionic acid ethyl ester (0.309 g, 0.576 mmol), phenol (0.163 g, 1.73 mmol), cesium carbonate (0.56 g, 1.72 mmol), copper (I) chloride (0.029 g, 0.293 mmol) and 2,2,6,6-tetramethyl-3,5-heptanedione (0.027 g, 0.147 mmol) in 1-methyl-2-pyrrolidinone (10 mL) is heated to 120° C. for 20 hours under N2. The reaction is cooled and quenched with 1 N HCl (20 mL). The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/ethyl acetate to afford 0.173 g (43%) of the title compound. Rf=0.55 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) M/z mass calculated for C32H29O35F3 550, found 551 (M+1, 100%).

後処理

  1. temperatureThe reaction is cooled
  2. customquenched with 1 N HCl (20 mL)
  3. additionThe mixture is then diluted with Et2O
  4. extractionextracted with water
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. customthe solvent is removed in vacuo
  7. customto afford crude product that
  8. customis absorbed on silica gel
  9. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-c48688ead529439ab9bd49708feeb1d1
出典データセット
uspto-grants-2009_10
特許番号
US07608639B2

反応ノート

読み込み中…