3,5-Dimethyl-4-hydroxybenzaldehyde → 3-(4-Hydroxy-3,5-dimethyl-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one

HRID 552278

反応式

HRID 552278 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][CH:14]=[CH:13][CH:12]=1)[CH3:2].[CH3:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([CH3:27])[C:25]=1[OH:26])[CH:21]=O>C(O)C.Cl.C(O)(C)C.O>[OH:26][C:25]1[C:24]([CH3:27])=[CH:23][C:20]([CH2:21][CH2:9][C:8]([C:6]2[S:7][C:3]([CH2:1][CH3:2])=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=2)=[O:10])=[CH:19][C:18]=1[CH3:17]

参加物

7

反応物 2

HCID 752223,5-Dimethyl-4-hydroxybenzaldehydeHCID 671661641-(5-Ethyl-4-phenyl-thiophen-2-yl)-ethanone

生成物 1

HCID 592489883-(4-Hydroxy-3,5-dimethyl-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one収率 58.2%

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-phenyl-thiophen-2-yl)-ethanone (64 mg, 0.278 mmol) and 3,5-dimethyl-4-hydroxybenzaldehyde (53 mg, 0.334 mmol) in ethanol (1.2 mL) and 5 N HCl in isopropanol (0.6 mL) is stirred at rt for 1 h. The dark green solution is diluted with water and extracted with EA. The organic extract is evaporated, dissolved in methanol (1 mL) and THF (1 mL), and treated with Pd/C (60 mg, 10% Pd). The slurry is hydrogenated under 1.4 bar of H2 for 1.5 h. The mixture is filtered over celite, the solvent is removed in vacuo and the crude product is purified on prep. TLC plates with heptane:EA 2:1 to give 3-(4-hydroxy-3,5-dimethyl-phenyl)-1-(5-ethyl-4-phenyl-thiophen-2-yl)-propan-1-one (59 mg) as a yellow oil; LC-MS: tR=1.11 min; 1H NMR (CDCl3): δ 7.58 (s, 1H), 7.46-7.30 (m, 5H), 6.85 (s, 2H), 4.56 (s, 1H), 3.18-3.10 (m, 2H), 2.97-2.86 (m, 4H), 2.22 (s, 6H), 1.30 (t, J=7.6 Hz, 3H).

後処理

  1. extractionextracted with EA
  2. extractionThe organic extract
  3. customis evaporated
  4. dissolutiondissolved in methanol (1 mL)
  5. additionTHF (1 mL), and treated with Pd/C (60 mg, 10% Pd)
  6. filtrationThe mixture is filtered over celite
  7. customthe solvent is removed in vacuo
  8. customthe crude product is purified on prep

出典と根拠

ORDレコード
ord-f9f4bea4cd2141c78ebf498dcad1bca1
出典データセット
uspto-grants-2011_05
特許番号
US07951794B2

関連ノート

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