(2E)-3-(furan-3-yl)prop-2-enoic acid → 3-(Oxolan-3-yl)propanoic acid

HRID 1011061ノート

反応式

HRID 1011061 の反応式
[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[C:8]([OH:10])=[O:9])=[CH:2]1.[H][H]>[Pd].C(OCC)(=O)C>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:2]1

参加物

5

反応物 2

HCID 643403(2E)-3-(furan-3-yl)prop-2-enoic acidHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 2840903-(Oxolan-3-yl)propanoic acid収率 95.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (2E)-3-(3-furanyl)-2-propenoic acid (4.75 g, 34.4 mmol) and 10% palladium on carbon (0.366 g, 3.44 mmol) in ethyl acetate (100 ml) was hydrogentated at atmospheric pressure and room temperature for 72 hours. Hydrogen uptake ˜1.4 L (expected 2.4 L). The catalyst was filtered through Celite and concentrated in vacuo to give a brown oil. Analysis by 1H-NMR showed that the some material still contained the furan ring. Hydrogenation was continued under the same conditions with fresh catalyst for a further 24 hours with additional hydrogen uptake of 400 ml. The catalyst was filtered through Celite and the filtrate concentrated in vacuo to afford the title compound as a colourless oil (4.73 g).

後処理

  1. filtrationThe catalyst was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customto give a brown oil
  4. filtrationThe catalyst was filtered through Celite
  5. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-a066e5dd958d4381b557ab085958f4c3
出典データセット
uspto-grants-2011_07
特許番号
US07977344B2

反応ノート

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