Methanol → 3-{5-[4-(dimethoxymethyl)phenoxy]-1-ethyl-1H-pyrazol-3-yl}benzonitrile

HRID 540762Notes

Reaction equation

HRID 540762 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)C.[CH2:8]([N:10]1[C:14]([O:15][C:16]2[CH:21]=[CH:20]C(C=O)=[CH:18][CH:17]=2)=[CH:13][C:12]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])=[N:11]1)[CH3:9].[CH3:32]O>>[CH3:1][O:4][CH:5]([O:7][CH3:32])[C:6]1[CH:20]=[CH:21][C:16]([O:15][C:14]2[N:10]([CH2:8][CH3:9])[N:11]=[C:12]([C:24]3[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=3)[C:27]#[N:28])[CH:13]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 772311493-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]benzonitrile

Product 1

HCID 671110533-{5-[4-(dimethoxymethyl)phenoxy]-1-ethyl-1H-pyrazol-3-yl}benzonitrileYield 77%

Conditions

Temperature
50 °C

Procedure

Acetic anhydride (0.24 mL, 3.3 mmol, 0.1 equiv) was added to a stirring solution of 3-[1-ethyl-5-(4-formylphenoxy)-1H-pyrazol-3-yl]benzonitrile (10.5 g, 33.0 mmol, 1 equiv) in methanol (66 mL). 4A molecular sieves were then added and the mixture was stirred at 50° C. for 3 hours. The sieves were filtered away and the filtrate was purified by flash chromatography (0-40% EtOAc:Hex) to give 3-{5-[4-(dimethoxymethyl)phenoxy]-1-ethyl-1H-pyrazol-3-yl}benzonitrile (77% yield). Calc'd (M+1) 364.2. Found: 364.1

Workup

  1. filtrationThe sieves were filtered away
  2. customthe filtrate was purified by flash chromatography (0-40% EtOAc:Hex)

Sources & evidence

ORD record
ord-59ed4eddf35344df9072c52c2bc83947
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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