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

HRID 376598

반응식

HRID 376598 반응식
[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

참가 물질

5

반응물 2

HCID 747102-Furancarboxylic acid, 5-methyl-HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 187800675-Methyloxolane-2-carboxylic acid수율 97.3%

시약·촉매·용매 2

HCID 23948Rhodium촉매HCID 8857Ethyl Acetate용매

실험 절차

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)].

후처리

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

출처 및 근거

ORD 기록
ord-5fe28c5f82214b858e2873896da57487
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020329

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