HCID 86662721, compound → HCID 66778291, compound

HRID 2090943Notes

Reaction equation

HRID 2090943 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([CH3:14])[C:11]([CH:15]=[O:16])=[N:10]2)[CH:6]=[CH:7][CH:8]=1.[CH:17]1([Mg]Br)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCCC1>[CH:17]1([CH:15]([C:11]2[C:12]([CH3:14])=[CH:13][N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:10]=2)[OH:16])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 86662721HCID 86662721, compound2×HCID 178419651HCID 178419651, compound

Product 1

HCID 66778291HCID 66778291, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (10 mL) of 1-(3-methoxyphenyl)-4-methyl-1H-pyrazole-3-carbaldehyde (0.84 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added dropwise under ice-cooling cyclohexylmagnesium bromide (7.0 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, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (0.62 g, 52%) 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
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

Sources & evidence

ORD record
ord-e76817afafda4a5691bd8e27a88f295a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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