2-Furancarboxylic acid, 5-methyl- → 5-Methyloxolane-2-carboxylic acid

HRID 376598

反応式

HRID 376598 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Rh]>[CH3:1][CH:2]1[O:6][CH:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3]1

参加物

5

反応物 2

HCID 747102-Furancarboxylic acid, 5-methyl-HCID 178418361HCID 178418361、化合物

生成物 1

HCID 187800675-Methyloxolane-2-carboxylic acid収率 97.3%

試薬・触媒・溶媒 2

HCID 23948Rhodium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 5-methyl-2-furoic acid (3.65g, 28.97mmol) in ethyl acetate (60ml) was hydrogenated over 5% rhodium on carbon (250mg) until hydrogen uptake ceased. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were concentrated in vacuo to yield the title compound as a pale yellow oil (3.67g, 97%); vmax (CH2Cl2) 3384, 3359, 1775, 1724 and 1355cm-1 ; δH (CDCl3, 250MHz) 1.35 (3H, d, J 6.1Hz), 1.53 (1H, m), 2.09 (1H, m), 2.17-2.40 (2H, m), 4.21 (1H, m) and 4.46 (1H, dd, J 8.9, 4.7Hz). [Mass spectrum: +ve ion (ammonia) MNH4+ (148)].

後処理

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated in vacuo

出典と根拠

ORDレコード
ord-5fe28c5f82214b858e2873896da57487
出典データセット
uspto-grants-2000_02
特許番号
US06020329

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