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Water → 3-(4-isopropoxyphenyl)-1-(2-methoxyethyl)-1H-pyrazole-4-carbaldehyde

HRID 526775
Notes
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Reaction equation

HRID 526775 reaction equation
Cl.[CH3:2][CH:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([CH:17]=[O:18])=[CH:15][NH:14][N:13]=2)=[CH:8][CH:7]=1)[CH3:4].C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][O:28][CH3:29].O>C(#N)C>[CH:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([CH:17]=[O:18])=[CH:15][N:14]([CH2:26][CH2:27][O:28][CH3:29])[N:13]=2)=[CH:8][CH:7]=1)([CH3:2])[CH3:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1784582693-(4-isopropoxyphenyl)-1H-pyrazole-4-carbaldehyde hydrochloride

Product 1

HCID 1176661203-(4-isopropoxyphenyl)-1-(2-methoxyethyl)-1H-pyrazole-4-carbaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
2.5 °C

Procedure

A mixture of 3-[4-(propan-2-yloxy)phenyl]-1H-pyrazole-4-carbaldehyde hydrochloride (400 mg, 1.5 mmol) and K2CO3 (655 mg, 4.6 mmol) in acetonitrile (6 ml) was stirred at 0-5° C. for 1 hr. 1-bromo-2-methoxyethane (195 mg, 1.4 mmol) was added and the reaction mixture was stirred at ambient temperature for 48 h. The reaction was poured into water (200 mL) and extracted with EtOAc (50 mL×3). The combined extracts was washed with brine (100 mL), dried and concentrated under vacuum (360 mg, yield 72%). The crude material was used in the next step without purification.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 48 h
  2. extractionextracted with EtOAc (50 mL×3)
  3. washThe combined extracts was washed with brine (100 mL)
  4. customdried
  5. concentrationconcentrated under vacuum (360 mg, yield 72%)
  6. customThe crude material was used in the next step without purification

Sources & evidence

ORD record
ord-805567eaa43440158fbc452578a633a7
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346761B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes