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Hydrochloric Acid → 4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzaldehyde

HRID 507954
Notes
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Reaction equation

HRID 507954 reaction equation
CN1CCNCC1.COCCO[Al-]OCCOC.[Na+].[C:20]([C:24]1[CH:28]=[C:27]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:26]([CH2:37][C:38]2[CH:47]=[CH:46][C:41]([C:42](OC)=[O:43])=[CH:40][CH:39]=2)[N:25]=1)([CH3:23])([CH3:22])[CH3:21].Cl>>[C:20]([C:24]1[CH:28]=[C:27]([CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:26]([CH2:37][C:38]2[CH:47]=[CH:46][C:41]([CH:42]=[O:43])=[CH:40][CH:39]=2)[N:25]=1)([CH3:23])([CH3:21])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 531671-MethylpiperazineHCID 16689465Sodium dihydrobis(2-methoxyethyl)aluminateHCID 23157206methyl 4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzoate

Product 1

HCID 231574034-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzaldehydeYield 92.3%

Procedure

1-Methylpiperazine (10.7 g, 107 mmol) was added dropwise to sodium dihydridobis(2-methoxyethoxy)aluminate (70% toluene solution, 25 g, 86.6 mmol) at 0° C. To the obtained solution was added methyl 4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzoate (1.65 g, 4.38 mmol) at 0° C. by small portions, and the mixture was further stirred at the same temperature for 1 hr. The reaction mixture was poured into 2 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (1.40 g, yield 92%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf88df4a9dc7441da5c7c4485b85c5c5
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07786165B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes