HCID 58136914, compound → HCID 58136949, compound

HRID 657970Notes

Reaction equation

HRID 657970 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:13]=[C:14]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])[CH:15]=1)[C:7](N(OC)C)=[O:8])[CH3:2].[CH2:22]([Mg]Br)[CH3:23]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7](=[O:8])[CH2:22][CH3:23])[CH:13]=[C:14]([S:16]([F:18])([F:21])([F:17])([F:19])[F:20])[CH:15]=1)[CH3:2]

Participants

4

Reactant 2

HCID 58136914HCID 58136914, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 58136949HCID 58136949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Ethoxy-N-methoxy-N-methyl-5-(pentafluorosulfanyl)benzamide (O3.062; 170 mg) was dissolved in absolute THF (5 ml), and ethylmagnesium bromide (0.65 ml; 2 M in diethyl ether) was added dropwise at 0° C. while stirring. After addition, the ice bath was removed and the mixture was stirred at RT for 2 h. Then further ethylmagnesium bromide (0.1 ml) was added and the mixture was stirred once again for 2 h. While cooling, 1 N hydrochloric acid was subsequently added dropwise, followed by water and ethyl acetate. The organic phase was removed and the aqueous phase was extracted twice more with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 150 mg of the desired compound were obtained.

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. stirringthe mixture was stirred at RT for 2 h
  4. additionThen further ethylmagnesium bromide (0.1 ml) was added
  5. stirringthe mixture was stirred once again for 2 h
  6. temperatureWhile cooling
  7. addition1 N hydrochloric acid was subsequently added dropwise
  8. customThe organic phase was removed
  9. extractionthe aqueous phase was extracted twice more with ethyl acetate
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-e00153716de84cb6bbffe8aa866d4e3c
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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