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 584437Notes

Reaction equation

HRID 584437 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3e231bb2802b4a80ada8f0f85667fe4a
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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