Hydrochloric Acid → HCID 57198439, 화합물

HRID 1464334노트

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HRID 1464334 반응식
[CH2:1]([O:3][C:4]([CH2:6][C:7](=[O:28])[CH:8]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[H-].[Na+].[CH:31](=O)[CH2:32][CH2:33][CH2:34][CH3:35].Cl>O1CCCC1.O>[O:28]=[C:7]([CH:8]=[CH:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8063PentanalHCID 24758Sodium hydrideHCID 2734128Ethyl 3-oxo-4-(triphenyl-lambda~5~-phosphanylidene)butanoate

생성물 1

HCID 57198439HCID 57198439, 화합물수율 40.2%

시약·촉매·용매 2

HCID 962Water촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

To a solution of (3-ethoxycarbonyl-2-oxopropylidene)triphenylphosphorane (5.0 g, 12.8 mmol) in tetrahydrofuran (THF, 50 ml) were added sodium hydride (60% dispersion in oil, 1.03 g, 25.6 mmol) and then pentanal (1.10 g, 12.8 mmol) followed by stirring. After addition of water (three drops), the mixture was heated at 45° C. for 1 hour. The reaction mixture was treated with dilute hydrochloric acid and extracted with ether. The organic layer was washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride, dried (MgSO4), and concentrated to dryness. The resulting residue was purified by column chromatography on silica gel. The column was eluted with dichloromethane-hexane (1:1 to 3:2) to give 1.02 g (40.0%) of the title compound as an oil. The 1H-NMR spectrum indicates that the product is a mixture of keto/enol isomers.

후처리

  1. extractionextracted with ether
  2. washThe organic layer was washed with aqueous saturated sodium bicarbonate and aqueous saturated sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was purified by column chromatography on silica gel
  6. washThe column was eluted with dichloromethane-hexane (1:1 to 3:2)

출처 및 근거

ORD 기록
ord-9b52cb9d3c7143298531813b01402c3c
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304565

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