Water → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(4,4-diethoxy-1-hydroxybut-2-ynyl)pyrazole

HRID 1108824

Reaction equation

HRID 1108824 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][CH3:6])[CH3:2].C([Li])CCC.[C:15]([C:17]1[C:21]([CH:22]=[O:23])=[CH:20][N:19]([C:24]2[C:29]([Cl:30])=[CH:28][C:27]([C:31]([F:34])([F:33])[F:32])=[CH:26][C:25]=2[Cl:35])[N:18]=1)#[N:16].O>O1CCCC1.CCOCC>[C:15]([C:17]1[C:21]([CH:22]([OH:23])[C:6]#[C:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])=[CH:20][N:19]([C:24]2[C:29]([Cl:30])=[CH:28][C:27]([C:31]([F:32])([F:34])[F:33])=[CH:26][C:25]=2[Cl:35])[N:18]=1)#[N:16]

Participants

7

Reactant 4

HCID 962WaterHCID 20858Propane, 1,1-diethoxy-HCID 184179813-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-formylpyrazoleHCID 178418339Butyllithium

Product 1

HCID 221208993-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(4,4-diethoxy-1-hydroxybut-2-ynyl)pyrazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of propionaldehyde diethyl acetal (0.0192 g) in anhydrous tetrahydrofuran (2 ml) cooled to -78° C. under an atmosphere of nitrogen was added dropwise n-butyl lithium (621 μl, 2.5M in hexanes) and the mixture was stirred for 10 minutes. 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-formylpyrazole (0.05 g) was added and stirring continued for 30 minutes. The reaction mixture was poured into water (5 ml) and ether (5 ml). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel (5 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a white foam.

Workup

  1. stirringstirring
  2. waitcontinued for 30 minutes
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (5 g)
  7. washeluted with dichloromethane
  8. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-6d0d47396d3044efabe037c46b2dced3
Source dataset
uspto-grants-2000_05
Patent number
US06069157

Linked notes

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