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

HRID 2299883ノート

反応式

HRID 2299883 の反応式
Cl[CH2:2][C:3]1[CH:22]=[C:21]([O:23][CH3:24])[C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[C:5]([O:25][CH3:26])[CH:4]=1.[OH:27]/[N:28]=[C:29](/[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)\[CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33].[H-].[Na+].Cl>CN(C)C=O.O>[CH3:26][O:25][C:5]1[CH:4]=[C:3]([CH:22]=[C:21]([O:23][CH3:24])[C:6]=1[O:7][CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14])[CH2:2][O:27]/[N:28]=[C:29](/[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)\[CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoateHCID 223446054-(4-Chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole

生成物 1

HCID 22344619methyl (4E)-4-[[3,5-dimethoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoate収率 66.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 4-(4-chloromethyl-2,6-dimethoxyphenoxymethyl)-5-methyl-2-phenyloxazole (1.00 g) and methyl E-4-hydroxyimino-4-phenylbutyrate (585 mg) in N,N-dimethylformamide (40 ml) was added sodium hydride (60% in oil, 115 mg) at 0° C. After stirring for 2 hours, the reaction mixture was poured into water, neutralized with 2N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4), and concentrated. The residue was purified by column chromatography on silica gel. Elution with ethyl acetate-hexane (1:3, v/v) gave methyl E-4-[3,5-dimethoxy-4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (970 mg, yield 65%) as a colorless oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel
  6. washElution with ethyl acetate-hexane (1:3

出典と根拠

ORDレコード
ord-045fa07c1810419b8860168e76b1ce6d
出典データセット
uspto-grants-2002_12
特許番号
US06495581B1

反応ノート

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