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

HRID 2299835노트

반응식

HRID 2299835 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-58eba6abe52e461992665b882c47fe4f
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495581B1

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