1,4-Cyclohexanedione → Methyl 2-(4-oxocyclohexylidene)propanoate

HRID 522237노트

반응식

HRID 522237 반응식
C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])C=CC=CC=1.[C:26]1(=[O:33])[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]1>C1(C)C=CC=CC=1>[O:33]=[C:26]1[CH2:27][CH2:28][C:29](=[C:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH2:30][CH2:31]1

참가 물질

4

반응물 2

HCID 125111,4-CyclohexanedioneHCID 10569721Methyl 2-(triphenyl-lambda~5~-phosphanylidene)propanoate

생성물 1

HCID 118274233Methyl 2-(4-oxocyclohexylidene)propanoate

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

A mixture of methyl 2-(triphenylphosphoranylidene)propanoate (2.5 g, 7.18 mmol) and cyclohexane-1,4-dione (1.609 g, 14.35 mmol) in toluene (25 mL) was stirred at 100° C. overnight and then concentrated in vacuo. The residue was triturated with a mixture of hexanes (100 mL) and ethyl acetate (100 mL), and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on Analogix IntelliFlash280 eluting with 0 to 50% ethyl acetate/hexanes to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.85 (p, J=1.5 Hz, 3H), 2.27-2.35 (m, 2H), 2.41 (dd, J=8.0, 5.8 Hz, 2H), 2.55-2.65 (m, 2H), 2.81-2.90 (m, 2H), 3.66 (s, 3H).

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with a mixture of hexanes (100 mL) and ethyl acetate (100 mL)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by flash chromatography on Analogix IntelliFlash280
  6. washeluting with 0 to 50% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-878ce4b42598475db3bca782a7a9cd74
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328112B2

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