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

HRID 584474노트

반응식

HRID 584474 반응식
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1.[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+].CN(C)C=O>C(OCC)(=O)C.CCCCCC.O>[C:29]1(/[C:22](=[N:21]/[O:20][CH2:19][C:18]2[CH:35]=[CH:36][C:15]([O:14][CH2:2][C:3]3[O:7][N:6]=[C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH:4]=3)=[CH:16][CH:17]=2)/[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27640575-(Chloromethyl)-3-phenylisoxazoleHCID 10946929methyl (4E)-4-[(4-hydroxyphenyl)methoxyimino]-4-phenylbutanoate

생성물 1

HCID 11826794methyl (4E)-4-phenyl-4-[[4-[(3-phenyl-1,2-oxazol-5-yl)methoxy]phenyl]methoxyimino]butanoate수율 68.1%

시약·촉매·용매 2

HCID 962Water용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A mixture of 5-(chloromethyl)-3-phenylisoxazole (238 mg), methyl E-4-(4-hydroxybenzyloxyimino)-4-phenylbutyrate (350 mg), potassium carbonate (310 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 13 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-phenyl-4-[4-(3-phenyl-5-isoxazolylmethoxy)benzyloxyimino]butyrate (358 mg, yield 62%) as a colorless oil from an ethyl acetate-hexane (1:4, 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-77d38f8e07bf4c62829df83af7b1bea2
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924300B2

반응 노트

불러오는 중…