Potassium Carbonate → Methyl E-4-{3-(4-cyanobenzyl)-5-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]pent-4-enyl}benzoate

HRID 1927418ノート

反応式

HRID 1927418 の反応式
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].Cl[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=2)=[CH:36][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8](/[CH:21]=[CH:22]/[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:47])([F:48])[F:49])=[CH:42][CH:41]=3)=[CH:38][CH:39]=2)[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:30][CH:31]=1)#[N:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 114599214-(4-Trifluoromethylphenyl)benzylchlorideHCID 57831354methyl E-4-[3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate

生成物 1

HCID 57831398Methyl E-4-{3-(4-cyanobenzyl)-5-[2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]pent-4-enyl}benzoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 300 mg (0.73 mmol) of methyl 4-[(4E)-3-(4-cyanobenzyl)-5-(2-hydroxyphenyl)pent-4-en-1-yl]benzoate in 30 ml of dry acetonitrile is mixed with 236.8 mg (0.87 mmol) of 4-(chloromethyl)-4′-(trifluoromethyl)biphenyl and 151 mg (1.09 mmol) of anhydrous potassium carbonate and 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 resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 331 mg (0.51 mmol, 70% of theory) of a solid are obtained.

後処理

  1. temperatureheated
  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
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3)
  8. custom331 mg (0.51 mmol, 70% of theory) of a solid are obtained

出典と根拠

ORDレコード
ord-26c7de5956774250b90fa808320963e3
出典データセット
uspto-grants-2012_05
特許番号
US08183271B2

反応ノート

読み込み中…