Water → HCID 178478537, compound

HRID 64631Notes

Reaction equation

HRID 64631 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.O.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 178519585HCID 178519585, compound

Product 1

HCID 178478537HCID 178478537, compoundYield 126.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.638 g of α,α-bis(4-chlorophenyl)-1H-pyrazole-3-methanol in 15 ml of trifluoroacetic acid was cooled to 0° C. Under a nitrogen atmosphere, 0.464 g of triethylsilane in 1 ml of methylene chloride was added. After stirring for 1 hour at 0° C., the mixture was poured into water, treated with sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate extract was dried, filtered, and evaporated to provide 428 mg of the title product (base) as a colorless oil. The residue was dissolved in ether, dry hydrogen chloride was added, and the title product was recovered by filtration providing white crystals with a melting point of 155°-165° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. customwas dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0063c170af4c4bb7b521065f60d438b8
Source dataset
uspto-grants-1986_09
Patent number
US04609666

Reaction notes

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