Ammonium Chloride → HCID 21700064, compound

HRID 1597419Notes

Reaction equation

HRID 1597419 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([Li])CCC.[CH3:26][O:27][CH2:28][C:29](OCC)=[O:30].[NH4+].[Cl-]>C1COCC1>[CH3:26][O:27][CH2:28][C:29](=[O:30])[CH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 77544Ethyl 2-methoxyacetateHCID 21700015HCID 21700015, compoundHCID 178418339Butyllithium

Product 1

HCID 21700064HCID 21700064, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 4-(4′-trifluoromethylphenyl)phenyl methyl sulfone (1.0 g, 3.33 mmol) in THF (50 mL) at −78° C. was treated with n-butyllithium (2.5M/hexanes, 1.4 mL, 3.50 mmol), stirred at −78° C. for 1.5 hours and then treated with ethyl methoxyacetate (0.78 mL, 6.66 mmol), stirred at −78° C. for three hours, treated with saturated NH4Cl solution, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), concentrated and purified on silica gel with 30-50% ethyl acetate/hexanes to provide 902 mg (73%) of the title compound as a white solid. MS (APCI) m/z 390 (M+NH4)+, 371 (M−H)−, 470 (M+Cl)−.

Workup

  1. stirringstirred at −78° C. for three hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified on silica gel with 30-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-df38204d9ca84073a8ea0fde1c56e259
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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