Methyl 5-(chloromethyl)-2-furoate → Methyl 5-methyl-2-furancarboxylate

HRID 376596

반응식

HRID 376596 반응식
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1>C(OCC)(=O)C.[Pd]>[CH3:2][C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1

참가 물질

4

반응물 1

HCID 75065Methyl 5-(chloromethyl)-2-furoate

생성물 1

HCID 137628Methyl 5-methyl-2-furancarboxylate수율 94%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 5-chloromethyl-2-furoate (5.0g, 28.7mmol) in ethyl acetate (40ml) was hydrogenated over 10% palladium on charcoal (50mg) for 3h. The catalyst was filtered off and washed with ethyl acetate. The combined filtrates were concentrated in vacuo and the residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexane to yield the title compound as a colourless oil (3.78g, 94%); vmax (CH2Cl2) 1725, 1534, 1522, 1437 and 1311cm-1 ; δH (CDCl3, 90MHz) 2.38 (3H, s), 3.86 (3H, s), 6.12 (1H, br d, J 4Hz) and 7.07 (1H, d, J 4Hz). [Mass spectrum: M+(140)].

후처리

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. customthe residue purified by chromatography on silica gel eluting with 10% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-e5864c8f3b0946adbdba3f81e27aa45c
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020329

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