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

반응식

HRID 552278 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

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

시약·촉매·용매 4

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매HCID 962Water용매HCID 3776Isopropanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f9f4bea4cd2141c78ebf498dcad1bca1
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951794B2

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