Hydrochloric Acid → HCID 86605885, compound

HRID 2221940Notes

Reaction equation

HRID 2221940 reaction equation
Cl[CH2:2][C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:16]=[CH:17][C:18]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[C:19]([CH:24]=3)[C:20]([O:22][CH3:23])=[O:21])[O:12][C:13]=2[CH3:14])=[C:5]([O:32][CH3:33])[CH:4]=1.[OH:34][C:35]1[C:39]([CH:40]=[O:41])=[CH:38][N:37]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[N:36]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH:40]([C:39]1[C:35]([O:34][CH2:2][C:3]2[CH:31]=[CH:30][C:6]([O:7][CH2:8][C:9]3[N:10]=[C:11]([C:15]4[CH:16]=[CH:17][C:18]([O:25][S:26]([CH3:29])(=[O:28])=[O:27])=[C:19]([CH:24]=4)[C:20]([O:22][CH3:23])=[O:21])[O:12][C:13]=3[CH3:14])=[C:5]([O:32][CH3:33])[CH:4]=2)=[N:36][N:37]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:38]=1)=[O:41]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86605733HCID 86605733, compoundHCID 178519806HCID 178519806, compound

Product 1

HCID 86605885HCID 86605885, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 5-{4-[(4-chloromethyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-(methanesulfonyloxy)benzoate (1.50 g), 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (0.56 g), potassium carbonate (0.41 g) and N,N-dimethylformamide (30 mL) was stirred at room temperature for 2 hrs. The reaction mixture was acidified by adding 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:3 to 1:1, v/v) to give methyl 5-{4-[(4-{[(4-formyl-1-phenyl-1H-pyrazol-3-yl)oxy]methyl}-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}-2-(methanesulfonyloxy)benzoate as pale-yellow crystals (0.80 g, yield 41%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 136-137° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:3 to 1:1

Sources & evidence

ORD record
ord-9589044f873a4af28ef71eaa7ba7f6d1
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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