Water → HCID 66971323, compound

HRID 2102327Notes

Reaction equation

HRID 2102327 reaction equation
C([O:8][C:9]1[NH:10][N:11]([CH:26]([CH3:28])[CH3:27])[C:12]([C:16]2[CH:25]=[CH:24][C:19]3[O:20][CH2:21][CH2:22][O:23][C:18]=3[CH:17]=2)(C=O)[CH:13]=1)C1C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([Mg]Br)=[CH:33][CH:32]=1.O.O1CCC[CH2:41]1>>[CH:26]([N:11]1[C:12]([C:16]2[CH:25]=[CH:24][C:19]3[O:20][CH2:21][CH2:22][O:23][C:18]=3[CH:17]=2)=[C:13]([CH2:41][C:34]2[CH:35]=[CH:36][C:31]([O:30][CH3:29])=[CH:32][CH:33]=2)[C:9](=[O:8])[NH:10]1)([CH3:27])[CH3:28]

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 86605410HCID 86605410, compoundHCID 178491912HCID 178491912, compound

Product 1

HCID 66971323HCID 66971323, compound

Procedure

To a solution of 3-benzyloxy-5-(2,3-dihydrobenzo[1,4]-dioxin-6-yl)-5-formyl-1-isopropyl-1H-pyrazole (0.19 g) in tetrahydrofuran (2 mL) was added a solution of 4-methoxyphenyl-magnesium bromide in tetrahydrofuran (1 mol/L, 0.60 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours. A small amount of water was added to the reaction mixture, and the mixture was purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran). The obtained compound was dissolved in ethanol (10 mL). Ten percent (10%) Palladium-carbon powder was added to the solution, and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. Dichloromethane was added to the reaction mixture, and the insoluble material was removed by filtration. The solvent of the filtrate was removed under reduced pressure, and ethanol and hexane were added to the residue. The precipitated material was collected by filtration and dried under reduced pressure to give the title compound (0.056 g).

Workup

  1. customthe mixture was purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran)
  2. dissolutionThe obtained compound was dissolved in ethanol (10 mL)
  3. additionTen percent (10%) Palladium-carbon powder was added to the solution
  4. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere overnight
  5. additionDichloromethane was added to the reaction mixture
  6. customthe insoluble material was removed by filtration
  7. customThe solvent of the filtrate was removed under reduced pressure, and ethanol and hexane
  8. additionwere added to the residue
  9. filtrationThe precipitated material was collected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-62c8707051d5406c9a377c4c9efef241
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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