Hydrochloric Acid → 1-(3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)ethanone

HRID 2221954Notes

Reaction equation

HRID 2221954 reaction equation
CON(C)[C:4]([C:6]1[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:25][C:26]=3[CH3:27])=[C:16]([O:34][CH3:35])[CH:15]=2)=[N:8][N:9]([CH3:11])[CH:10]=1)=[O:5].[CH3:37][Mg]Br.Cl>O1CCCC1>[CH3:35][O:34][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[O:20][CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:25][C:26]=1[CH3:27])[CH2:13][O:12][C:7]1[C:6]([C:4](=[O:5])[CH3:37])=[CH:10][N:9]([CH3:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23076606HCID 23076606, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 692163781-(3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)ethanoneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methyl-3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carboxamide (3.00 g) in tetrahydrofuran (30 mL) was slowly added methylmagnesium bromide (1.0 M tetrahydrofuran solution, 15 mL) at 0° C., and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 1-(3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazol-4-yl)ethanone (2.65 g, yield 97%) as colorless crystals. The crystals were recrystallized from acetone-hexane. melting point: 170-171° C.

Workup

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ed18bd96434f4b609405958185186572
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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