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 2299793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299793
[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

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 74505Methyltriphenyliphosphonium bromideKatalysator

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-59cfe1ccbb0b4183a045e011928ebe47
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495581B1

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