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

HRID 522237ノート

反応式

HRID 522237 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 118274233Methyl 2-(4-oxocyclohexylidene)propanoate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-878ce4b42598475db3bca782a7a9cd74
出典データセット
uspto-grants-2016_05
特許番号
US09328112B2

反応ノート

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