Hydrochloric Acid → ethyl (2Z)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-2-[3-(1-phenylethenyl)phenyl]acetate

HRID 584437노트

반응식

HRID 584437 반응식
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].C(C1C=C(/[C:21](=[N:27]/[O:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]3[N:39]=[C:40]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[O:41][C:42]=3[CH3:43])=[CH:32][CH:31]=2)/[C:22]([O:24][CH2:25][CH3:26])=[O:23])C=CC=1)(=O)C1C=CC=CC=1.Cl.[C:51](OCC)(=O)C.[CH3:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62].O1C[CH2:66][CH2:65][CH2:64]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:43][C:42]1[O:41][C:40]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[N:39][C:38]=1[CH2:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][O:28]/[N:27]=[C:21](/[C:64]2[CH:65]=[CH:66][CH:3]=[C:2]([C:5]([C:59]3[CH:58]=[CH:57][CH:62]=[CH:61][CH:60]=3)=[CH2:51])[CH:1]=2)\[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:31][CH:32]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2회HCID 21226206Ethyl acetate hexaneHCID 22344584ethyl (2Z)-2-(3-benzoylphenyl)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]acetateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 22344588ethyl (2Z)-2-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-2-[3-(1-phenylethenyl)phenyl]acetate수율 79%

시약·촉매·용매 1

HCID 74505Methyltriphenyliphosphonium bromide촉매

실험 절차

Potassium tert-butoxide (328 mg) was added to a mixture of methyltriphenylphosphonium bromide (1.14 g) and tetrahydrofuran (10 ml) under nitrogen atmosphere and stirred at room temperature for 1 hour. A solution of ethyl Z-2-(3-benzoylphenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (1.12 g) in tetrahydrofuran (10 ml) was added dropwise, stirred further for 3 hours, dilute hydrochloric acid was added 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 ethyl Z-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-2-[3-(1-phenylvinyl)phenyl]acetate (880 mg, yield 79%) as a pale brown oil from an ethyl acetate-hexane (1:4, v/v)-eluted fraction.

후처리

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

출처 및 근거

ORD 기록
ord-3e231bb2802b4a80ada8f0f85667fe4a
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924300B2

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