Hydrochloric Acid → HCID 59553525, compound

HRID 1170939Notes

Reaction equation

HRID 1170939 reaction equation
CON(C)[C:4](=[O:17])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1.[C:19]1([CH3:27])[CH:24]=[CH:23][CH:22]=[C:21]([Mg]Br)[CH:20]=1.Cl.O>C1COCC1.C(OCC)(=O)C>[C:19]1([CH3:27])[CH:24]=[CH:23][CH:22]=[C:21]([C:4](=[O:17])[CH2:5][CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 59553705HCID 59553705, compoundHCID 178425413HCID 178425413, compound

Product 1

HCID 59553525HCID 59553525, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.4 g (1.5 mmol) N-Methoxy-N-methyl-3-(4-trifluoromethyl-phenyl)-propionamide in 7 mL THF under argon at 0° C., was added dropwise 3.062 ml (3.1 mmol) m-Tolylmagnesiumbromid (1M in THF). The reaction mixture was stirred for 15 minutes at 0° C. and at RT for 50 minutes, cooled to 0° C. and acidified with 1N HCl to pH 1-2. Water and ethyl acetate were added and the water phase was extracted twice with ethyl acetate. The organic phases were dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude oil was purified with flash column chromatography on silica gel eluting with a gradient formed from heptane and ethylacetate to provide 0.36 g (81%) of title compound as colorless oil. MS (m/e): 293.0 (MH+).

Workup

  1. temperaturecooled to 0° C.
  2. extractionthe water phase was extracted twice with ethyl acetate
  3. dry with materialThe organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude oil was purified with flash column chromatography on silica gel eluting with a gradient
  7. customformed from heptane and ethylacetate

Sources & evidence

ORD record
ord-bb978ac27b414328a34553fdbc3128ab
Source dataset
uspto-grants-2010_11
Patent number
US07829563B2

Reaction notes

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