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

HRID 584481ノート

反応式

HRID 584481 の反応式
ClCC1N=[C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)OC=1C.[OH:14][C:15]1[CH:36]=[CH:35][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)\[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:43][N:44](C)[CH:45]=[O:46].[C:48](OCC)(=O)[CH3:49].[CH3:54]CCCCC>O>[CH3:48][C:49]1[O:46][C:45]([CH2:5][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[N:44][C:43]=1[CH2:54][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20]/[N:21]=[C:22](/[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)\[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:35][CH:36]=1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 50764914-(Chloromethyl)-5-methyl-2-(thiophen-2-yl)-1,3-oxazoleHCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoateHCID 21226206Ethyl acetate hexane

生成物 1

HCID 22344623methyl (4E)-4-[[4-[[5-methyl-2-(thiophen-2-ylmethyl)-1,3-oxazol-4-yl]methoxy]phenyl]methoxyimino]-4-phenylbutanoate収率 63%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 4-(chloromethyl)-5-methyl-2-(2-thienyl)oxazole (376 mg), methyl E-4-[(4-hydroxybenzyloxy)imino]-4-phenylbutyrate (500 mg), potassium carbonate (442 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 40 hours. 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-(2-thenyl)-4-oxazolylmethoxy]benzyloxyimino]-4-phenylbutyrate (495 mg, yield 63%) as a colorless oil from an ethyl acetate-hexane (1:5, v/v)-eluted fraction.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-a9663b748db64264811de2b0c6e62dbe
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

反応ノート

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