Tetrahydrofuran → HCID 21188136, compound

HRID 1383599Notes

Reaction equation

HRID 1383599 reaction equation
[C:1]([C:4]1[C:5]([C:21]#[N:22])=[N:6][N:7]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[CH:8]=1)(=O)[CH3:2].S([O-])([O-])(=O)=O.[Na+].[Na+].O1CCC[CH2:31]1>C1(C)C=CC=CC=1.CCOCC>[C:21]([C:5]1[C:4]([C:1]([CH3:31])=[CH2:2])=[CH:8][N:7]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:6]=1)#[N:22]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 21188131HCID 21188131, compound

Product 1

HCID 21188136HCID 21188136, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-acetyl-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (0.75 g) in tetrahydrofuran (5 ml) cooled to −40° C. under an atmosphere of nitrogen was added μ-chloro-μ-methylene-[bis(cyclopentadienyl)titanium]dimethylaluminium (5.18 ml of a 0.5M solution in toluene) and the mixture was stirred for 15 minutes then allowed to warm to room temperature. After 2 hours at room temperature 0.1M aqueous sodium sulphate solution was added dropwise until effervescence ceased. The reaction mixture was diluted with ether (50 ml), washed with aqueous sodium sulphate solution, dried and evaporated. The residue was purified by column chromatography on silica gel eluted with dichloromethane: hexane (1:1). Combination and evaporation of suitable fractions provided the title compound as a tan solid m.p. 63-64° C.

Workup

  1. washwashed with aqueous sodium sulphate solution
  2. customdried
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluted with dichloromethane: hexane (1:1)
  6. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-24d2c605e3744ec8a03580e4de25456f
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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