Hexachloroethane → HCID 59739604, compound

HRID 1192950Notes

Reaction equation

HRID 1192950 reaction equation
[CH:1]1([C:4]2[C:8]([CH2:9][S:10]([C:13]3[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][N:14]=3)(=[O:12])=[O:11])=[C:7]([CH3:20])[O:6][N:5]=2)[CH2:3][CH2:2]1.CC(C)([O-])C.[K+].[Cl:27]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.O>[Cl:27][CH:9]([S:10]([C:13]1[CH2:17][C:16]([CH3:18])([CH3:19])[O:15][N:14]=1)(=[O:11])=[O:12])[C:8]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][O:6][C:7]=1[CH3:20]

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 23665647Potassium tert-butoxideHCID 59739594HCID 59739594, compound

Product 1

HCID 59739604HCID 59739604, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-Cyclopropyl-4-(5,5-dimethyl-4,5-dihydroisoxazol-3-ylsulfonylmethyl)-5-methyl-isoxazole (108 mg, 0.36 mmol) was dissolved in THF (5 ml) under nitrogen. The solution was cooled to −78° C. and potassium tert-butoxide (0.4 ml, 0.4 mmol) added, followed by hexachloroethane (90 mg, 0.4 mmol). The solution was allowed to warm to room temperature, diluted with water (20 ml) and extracted with ethyl acetate (3×15 ml). The combined organic phases were dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (Compound No. 3.07 of Table 29) as a white solid (53 mg, 44% yield).

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8d0aa8f5b8cc4a8880248a442373021b
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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