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

HRID 584473

反応式

HRID 584473 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:23]=[CH:22][C:18]([CH2:19][O:20][NH2:21])=[CH:17][CH:16]=1.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]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:25](/[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)\[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:23]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 141190Benzenebutanoic acid, gamma-oxo-, methyl esterHCID 517045Sodium AcetateHCID 223445934-(5-Methyl-2-phenyl4-oxazolylmethoxy)benzyloxyamine

生成物 1

HCID 11081404methyl (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate収率 76%

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 4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyamine (1.00 g), methyl 4-oxo-4-phenylbutyrate (619 mg), acetic acid (0.553 ml), sodium acetate (528 mg) and methanol (20 ml) was heated to reflux for 19 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-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (1.18 g, yield 76%) as a colorless oil from an ethyl acetate-hexane (2:9, v/v)-eluted fraction.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 19 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-4580bc1efa6e471993dcf23b63b0543c
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

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