HCID 86662724, compound → HCID 66778051, compound

HRID 2090952Notes

Reaction equation

HRID 2090952 reaction equation
[CH2:1]([C:3]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[N:4]=1)[CH3:2].[CH:18]1([Mg]Br)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH:18]1([CH:8]([C:7]2[C:3]([CH2:1][CH3:2])=[N:4][N:5]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=3)[CH:6]=2)[OH:9])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 86662724HCID 86662724, compound2×HCID 178419651HCID 178419651, compound

Product 1

HCID 66778051HCID 66778051, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 mL) of 3-ethyl-1-(3-methoxyphenyl)-1H-pyrazole-4-carbaldehyde (1.9 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise under ice-cooling cyclohexylmagnesium bromide (12.0 mL, 1M tetrahydrofuran solution). After the completion of the dropwise addition, the ice bath was removed, and the mixture was stirred at room temperature for 15 min. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure to give a crude product (2.6 g, quantitative) of the title object compound as a pale-yellow oil.

Workup

  1. additionwas added dropwise under ice-
  2. additionAfter the completion of the dropwise addition
  3. customthe ice bath was removed
  4. additionTo the reaction mixture was added aqueous ammonium chloride solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-04d634f8df114cb781bfc55862e8bb7f
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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