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

HRID 612301

反応式

HRID 612301 の反応式
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

参加物

4

反応物 1

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

生成物 1

HCID 137628Methyl 5-methyl-2-furancarboxylate収率 94%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of methyl 5-chloromethyl-2-furoate (5.0 g, 28.7 mmol) in ethyl acetate (40 ml) was hydrogenated over 10% palladium on charcoal (50 mg) for 3 h. 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 (3.78 g, 94%); νmax (CH2Cl2) 1725, 1534, 1522, 1437 and 1311 cm-1 ; δH (CDCl3, 90 MHz) 2.38 (3 H, s), 3.86 (3 H, s), 6.12 (1 H, br d, J 4 Hz) and 7.07 (1 H, d, J 4 Hz). [Mass spectrum: M+ (140)].

後処理

  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

出典と根拠

ORDレコード
ord-5c1870501952413eab352dad8fe7b7ce
出典データセット
uspto-grants-1999_12
特許番号
US06001997

関連ノート

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