Potassium Carbonate → tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-{[4-(trifluoromethoxy)-benzyl]oxy}phenyl)but-3-en-1-yl]benzoate

HRID 1920594ノート

反応式

HRID 1920594 の反応式
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:22][C:23](=[O:54])[CH2:24][C:25]1([CH2:28][CH2:29][CH:30](/[CH:45]=[CH:46]/[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[OH:53])[CH2:31][C:32]2[CH:44]=[CH:43][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:34][CH:33]=2)[CH2:27][CH2:26]1)[CH3:21]>C(#N)C>[CH2:20]([O:22][C:23](=[O:54])[CH2:24][C:25]1([CH2:28][CH2:29][CH:30](/[CH:45]=[CH:46]/[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[O:53][CH2:8][C:7]2[CH:10]=[CH:11][C:4]([O:3][C:2]([F:13])([F:12])[F:1])=[CH:5][CH:6]=2)[CH2:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:43][CH:44]=2)[CH2:26][CH2:27]1)[CH3:21]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzeneHCID 57965746tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate

生成物 1

HCID 57965772tert-Butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-{[4-(trifluoromethoxy)-benzyl]oxy}phenyl)but-3-en-1-yl]benzoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

118 mg (0.46 mmol) of 4-trifluoromethoxybenzyl bromide and 98 mg (0.71 mmol) of anhydrous potassium carbonate are added to a solution of 170 mg (0.36 mmol) of tert-butyl 4-[(3E)-2-{2-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]ethyl}-4-(2-hydroxyphenyl)but-3-en-1-yl]benzoate in 3 ml of dry acetonitrile, and the mixture is heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). This gives 155 mg (67% of theory) of a colorless oil.

後処理

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated

出典と根拠

ORDレコード
ord-a4c7cf1e02fa4836abbfab62449e75ab
出典データセット
uspto-grants-2012_05
特許番号
US08168821B2

反応ノート

読み込み中…