Ethanol → 1-Cyclopentyl-3-(4-methoxyphenyl)propane-1,3-dione

HRID 81012

반응식

HRID 81012 반응식
[H-].[Na+].C(O)C.[CH:6]1([C:11]([O:13]C)=O)[CH2:10][CH2:9][CH2:8][CH2:7]1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=1>C1COCC1>[CH:6]1([C:11](=[O:13])[CH2:24][C:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[O:25])[CH2:7][CH2:8][CH2:9][CH2:10]1

참가 물질

6

반응물 4

HCID 702EthanolHCID 74764'-MethoxyacetophenoneHCID 24758Sodium hydrideHCID 78365Methyl cyclopentanecarboxylate

생성물 1

HCID 669270051-Cyclopentyl-3-(4-methoxyphenyl)propane-1,3-dione수율 56%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydride (1.378 g, 59.9 mmol, 60% suspension in mineral oil) and ethanol (2.0 mL) were added to a solution of methyl cyclopentanecarboxylate (6.14 g, 47.9 mmol) and 1-(4-methoxyphenyl)ethanone (6.00 g, 40.0 mmol) in THF (200 mL). The mixture was heated to reflux for 11 h, quenched with water (100 mL) and acidified to pH˜2 with 1 N HCl. The THF solvent was evaporated in vacuo. The residue was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with brine (25 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with hexanes and small amount of toluene and eluting with 0-15% ethyl acetate in hexanes, gave 1-cyclopentyl-3-(4-methoxyphenyl)propane-1,3-dione as yellow liquid (5.494 g, 56% yield). MS (ES+) m/z: 247 (M+H); LC retention time: 4.510 and 3.578 min, likely a mixture of keto and enol forms (analytical HPLC Method A).

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 11 h
  3. customquenched with water (100 mL)
  4. customThe THF solvent was evaporated in vacuo
  5. extractionThe residue was extracted with ethyl acetate (3×100 mL)
  6. washThe combined extracts were washed with brine (25 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. washeluting with 0-15% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-870cedaf153147b0848b952ce5ed12c7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846673B2

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