Ethanol → ethyl (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvate

HRID 1740917ノート

反応式

HRID 1740917 の反応式
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:27]=[CH:26][C:18](/[CH:19]=[CH:20]/[C:21](=[O:25])[C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.[CH2:28](O)[CH3:29].S(=O)(=O)(O)O>O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:27]=[CH:26][C:18](/[CH:19]=[CH:20]/[C:21](=[O:25])[C:22]([O:24][CH2:28][CH3:29])=[O:23])=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 18546125(E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvic acid

生成物 1

HCID 10971201ethyl (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvate収率 86%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvic acid (1.3 g) and ethanol (50 ml) was added conc. sulfuric acid (0.1 ml). The mixture was heated for 8 hours under reflux, then the reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent. The residue was subjected to a silica gel column chromatography. From the fractions eluted with ethyl acetate-hexane (1:3, v/v), ethyl (E)-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzylidenepyruvate (1,2 g, 86%) was obtained. Recrystallization from ethyl acetate-hexane gave pale yellow prisms. Melting point: 110-111° C.

後処理

  1. temperatureThe mixture was heated for 8 hours
  2. temperatureunder reflux
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationby distilling off the solvent
  7. washFrom the fractions eluted with ethyl acetate-hexane (1:3

出典と根拠

ORDレコード
ord-54a49b5354a644c29ee89886736a8354
出典データセット
uspto-grants-1999_10
特許番号
US05972970

反応ノート

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