3,5-Dimethyl-4-hydroxybenzaldehyde → 1-(5-Ethyl-4-p-tolyl-thiophen-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one

HRID 552293ノート

反応式

HRID 552293 の反応式
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[CH3:2].[CH3:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([CH3:28])[C:26]=1[OH:27])[CH:22]=O>C(O)C.Cl.C(O)(C)C.O>[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH2:9][CH2:22][C:21]2[CH:24]=[C:25]([CH3:28])[C:26]([OH:27])=[C:19]([CH3:18])[CH:20]=2)=[CH:5][C:4]=1[C:11]1[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=1)[CH3:2]

参加物

7

反応物 2

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 671663071-(5-Ethyl-4-p-tolyl-thiophen-2-yl)-ethanone

生成物 1

HCID 592489921-(5-Ethyl-4-p-tolyl-thiophen-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one収率 105.7%

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒

実験手順

A solution of 1-(5-ethyl-4-p-tolyl-thiophen-2-yl)-ethanone (28 mg, 0.115 mmol) and 3,5-dimethyl-4-hydroxybenzaldehyde (26 mg, 0.172 mmol) in ethanol (1.5 mL) and 5 N HCl in isopropanol (0.3 mL) is stirred at rt for 18 h. The solution is diluted with water and extracted with EA. The organic extract is evaporated, dissolved in methanol (3 mL) and THF (3 mL) and treated with Pd/C (30 mg, 10% Pd). The slurry is stirred under 1.5 bar of H2 for 18 h. The mixture is filtered, the solvent of the filtrate is removed in vacuo and the crude product is purified by prep. HPLC to give 1-(5-ethyl-4-p-tolyl-thiophen-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-propan-1-one (46 mg) as a colourless oil; LC-MS: tR=1.13 min, [M+1]+=379.22.

後処理

  1. extractionextracted with EA
  2. extractionThe organic extract
  3. customis evaporated
  4. dissolutiondissolved in methanol (3 mL)
  5. additionTHF (3 mL) and treated with Pd/C (30 mg, 10% Pd)
  6. filtrationThe mixture is filtered
  7. customthe solvent of the filtrate is removed in vacuo
  8. customthe crude product is purified by prep

出典と根拠

ORDレコード
ord-aad9c69b0d7b4d698e683df1e79cc9c3
出典データセット
uspto-grants-2011_05
特許番号
US07951794B2

反応ノート

読み込み中…