Ammonium Chloride → HCID 17985409, compound

HRID 910062Notes

Reaction equation

HRID 910062 reaction equation
C(O[CH:6]([O:17]CCCC)[C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N+:14]([O-])=O)CCC.[CH:22]([Mg]Br)=[CH2:23].[Cl-].[NH4+]>O1CCCC1>[CH3:13][C:11]1[CH:10]=[C:9]2[C:8](=[C:7]([CH:6]=[O:17])[CH:12]=1)[NH:14][CH:23]=[CH:22]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 17985768HCID 17985768, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 17985409HCID 17985409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Dissolve 2-Dibutoxymethyl-4-methyl-1-nitrobenzene (13.957 g, 47.373 mmol) in anhydrous tetrahydrofuran (474 mL) under nitrogen, and cool the solution to −40° C. Add vinylmagnesium bromide (190 mL, 190 mmol, 1.0 M in tetrahydrofuran) at 40° C. with stirring. Stir the reaction mixture for 40 minutes and add saturated aqueous ammonium chloride. Extract the aqueous layer with ethyl acetate. Combine the organic layers, dry over sodium sulfate, filter, and concentrate. Dissolve the residue in tetrahydrofuran (160 mL) and cool to 0° C. Add aqueous 0.5 molar hydrochloric acid (20 mL) and stir the mixture at 0° C. for 1 hour. Add saturated aqueous sodium hydrogen carbonate (200 mL) and extract the aqueous layer with ethyl acetate (3×200 mL). Combine the organic layers, dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure and purify by flash column chromatography (silica gel, 5% ethyl acetate/hexane) to give the title compound as a white solid.

Workup

  1. extractionExtract the aqueous layer with ethyl acetate
  2. dry with materialdry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. dissolutionDissolve the residue in tetrahydrofuran (160 mL)
  6. temperaturecool to 0° C
  7. stirringAdd aqueous 0.5 molar hydrochloric acid (20 mL) and stir the mixture at 0° C. for 1 hour
  8. extractionAdd saturated aqueous sodium hydrogen carbonate (200 mL) and extract the aqueous layer with ethyl acetate (3×200 mL)
  9. dry with materialCombine the organic layers, dry over anhydrous sodium sulfate
  10. filtrationfilter
  11. concentrationconcentrate under reduced pressure
  12. custompurify by flash column chromatography (silica gel, 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0f65ebac90984eec8e47fceccb59b333
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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