Hydrochloric Acid → HCID 69216299, compound

HRID 2221955Notes

Reaction equation

HRID 2221955 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[C:12]([CH:13]=[O:14])=[CH:11][N:10]([CH3:15])[N:9]=1.[CH3:33][Mg]Br.Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[C:12]([CH:13]([OH:14])[CH3:33])=[CH:11][N:10]([CH3:15])[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86605889HCID 86605889, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 69216299HCID 69216299, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[3-methoxy-4-(5-methyl-2-phenyl-1,3-oxazol-4-ylmethoxy)benzyl]oxy}-1-methyl-1H-pyrazole-4-carbaldehyde (0.45 g) in tetrahydrofuran (10 mL) was slowly added methylmagnesium bromide (3.0 M diethyl ether solution, 0.5 mL) at 0° C., and the mixture was stirred for 1 hr. 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)ethanol (0.38 g, yield 81%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 94-95° 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-568f6438f7c4413cadb3029b097bf7a9
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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