Diethyl Ether → HCID 21072857, compound

HRID 2223105Notes

Reaction equation

HRID 2223105 reaction equation
C(O[C:4](=[O:17])[NH:5][C:6]1[CH:11]=CC(OC)=[CH:8][C:7]=1[C:14](=[O:16])[CH3:15])C.[CH3:18][Mg]I.[Cl-].[NH4+].[CH2:23]([O:25][CH2:26][CH3:27])C>C1COCC1>[CH3:23][O:25][C:26]1[CH:27]=[CH:11][C:6]2[O:5][C:4](=[O:17])[NH:16][C:14]([CH3:15])([CH3:18])[C:7]=2[CH:8]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 13365077Ethyl (2-acetyl-4-methoxyphenyl)carbamateHCID 178418373HCID 178418373, compound

Product 1

HCID 21072857HCID 21072857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

47.4 g (0.2 mol) of ethyl(2-acetyl-4-methoxyphenyl)carbamate, dissolved in 275 mL of THF, are added dropwise to a solution of 0.5 mol of methylmagnesium iodide in 200 mL of diethyl ether while cooling so that the temperature does not exceed 0° C. The mixture is stirred for 30 minutes at ambient temperature and then for 2 hours at reflux temperature. The reaction mixture is poured onto ice and combined with ammonium chloride. After the organic phase has been separated off, it is repeatedly extracted with ethyl acetate. The organic phases are combined, washed with water, dried with sodium sulfate, and evaporated down. The residue is dissolved in methanol and the solution is evaporated down and then combined with water. The precipitate formed is separated off, washed with water and recrystallized from toluene. Yield: 31.1 g (75%); m.p.=178° C.-180° C.

Workup

  1. temperaturewhile cooling so that the temperature
  2. customdoes not exceed 0° C
  3. temperaturefor 2 hours at reflux temperature
  4. additionThe reaction mixture is poured onto ice
  5. customAfter the organic phase has been separated off
  6. extractionit is repeatedly extracted with ethyl acetate
  7. washwashed with water
  8. dry with materialdried with sodium sulfate
  9. customevaporated down
  10. dissolutionThe residue is dissolved in methanol
  11. customthe solution is evaporated down
  12. customThe precipitate formed
  13. customis separated off
  14. washwashed with water
  15. customrecrystallized from toluene

Sources & evidence

ORD record
ord-63687336904b464f94c069d9ca60cefd
Source dataset
uspto-grants-2008_05
Patent number
US07375104B2

Reaction notes

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