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Hydrochloric Acid → HCID 11016373, compound

HRID 2299881
Notes
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Reaction equation

HRID 2299881 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:10][C:11]=1[CH3:12].[OH:23]/[N:24]=[C:25](/[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)\[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29].[H-].[Na+].Cl>CN(C)C=O.O>[CH3:12][C:11]1[O:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][C:7]=1[CH2:6][O:5][C:4]1[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=1[CH2:2][O:23]/[N:24]=[C:25](/[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)\[CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 110990364-(2-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 12137371methyl (4E)-4-hydroxyimino-4-phenylbutanoate

Product 1

HCID 11016373HCID 11016373, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(2-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (1.50 g) and methyl E-4-hydroxyimino-4-phenylbutyrate (990 mg) in N,N-dimethylformamide (40 ml) was added sodium hydride (60% in oil, 200 mg) at 0° C. After stirring for 2 hours, the reaction mixture was poured into water, neutralized with 2N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried (MgSO4), and concentrated. The residue was purified by column chromatography on silica gel. Elution with ethyl acetate-hexane (1:4, v/v) gave methyl E-4-[2-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-4-phenylbutyrate (1.65 g, yield 71%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel
  6. washElution with ethyl acetate-hexane (1:4, v/v)

Sources & evidence

ORD record
ord-e79420c8b554401980988225cfc0fc48
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06495581B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes