2,4-Dimethoxybenzaldehyde → HCID 66971332, compound

HRID 2102328Notes

Reaction equation

HRID 2102328 reaction equation
C([O:8][C:9]1[C:13](Br)=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:11]([CH:23]([CH3:25])[CH3:24])[N:10]=1)C1C=CC=CC=1.C([Li])CCC.[CH3:31][O:32][C:33]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:34]=1[CH:35]=O>O1CCCC1>[CH:23]([N:11]1[C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[C:13]([CH2:35][C:34]2[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[CH:40][C:33]=2[O:32][CH3:31])[C:9](=[O:8])[NH:10]1)([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 691752,4-DimethoxybenzaldehydeHCID 23079539HCID 23079539, compoundHCID 178418339Butyllithium

Product 1

HCID 66971332HCID 66971332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-benzyloxy-4-bromo-1-isopropyl-5-(4-methoxyphenyl)-1H-pyrazole in tetrahydrofuran (2 mL) was added n-butyllithium (2.6 mol/L hexane solution, 0.89 mL) at −78° C. under argon atmosphere, and the mixture was stirred for 30 minutes. A solution of 2,4-dimethoxybenzaldehyde (0.51 g) in tetrahydrofuran (2 mL) was added to the reaction mixture, and the mixture was stirred at −78° C. for 1 hour. The reaction mixture was directly purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran). The obtained semi purified [3-benzyloxy-1-isopropyl-5-(4-methoxyphenyl)-1H-pyrazol-4-yl (2,4-dimethoxyphenyl)methanol was dissolved in ethanol (9 mL), and a catalytic amount of 10% palladium-carbon powder was added to the solution. 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, and diethyl ether and hexane were added to the residue. The insoluble material was collected by filtration and dried under reduced pressure to give the title compound (0.09 g).

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 hour
  2. customThe reaction mixture was directly purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran)
  3. customThe obtained semi purified [3-benzyloxy-1-isopropyl-5-(4-methoxyphenyl)-1H-pyrazol-4-yl (2,4-dimethoxyphenyl)methanol
  4. dissolutionwas dissolved in ethanol (9 mL)
  5. additiona catalytic amount of 10% palladium-carbon powder was added to the solution
  6. stirringThe mixture was stirred at room temperature under a hydrogen atmosphere overnight
  7. additionDichloromethane was added to the reaction mixture
  8. customthe insoluble material was removed by filtration
  9. customThe solvent of the filtrate was removed
  10. additiondiethyl ether and hexane were added to the residue
  11. filtrationThe insoluble material was collected by filtration
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-0dfc5f80cf11439ca4505da7cc91d839
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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