Acetic Acid → methyl (4E)-4-[[3-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate

HRID 584464

反応式

HRID 584464 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:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19][NH2:20].O=[C:25]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.CO>[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:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[CH2:18][O:19]/[N:20]=[C:25](/[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)\[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 517045Sodium AcetateHCID 109249463-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine

生成物 1

HCID 11762628methyl (4E)-4-[[3-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate収率 61%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

After a mixture of 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (600 mg), methyl 4-oxo-4-phenylbutyrate (371 mg), acetic acid (0.331 ml), sodium acetate (317 mg) and methanol (20 ml) was heated to reflux for 40 hours, the mixture was cooled to room temperature. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (570 mg, yield 61%) as a colorless oil from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 40 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-9355021df79947bb854939804521962e
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

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