Diethyl Ether → HCID 21072857, compound

HRID 1372899Notes

Reaction equation

HRID 1372899 reaction equation
C([C:4]1C=C(OC)[CH:7]=[CH:6][C:5]=1[NH:12][C:13](=[O:17])[O:14][CH2:15][CH3:16])(=O)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:4][C:5]2[O:12][C:13](=[O:17])[NH:14][C:15]([CH3:16])([CH3:18])[C:6]=2[CH:7]=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) ethyl (2-acetyl-4-methoxy-phenyl)-carbamate, dissolved in 275 mL THF, are added dropwise to a solution of 0.5 mol methylmagnesium iodide in 200 mL 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 sulphate 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 recrystallised from toluene. Yield: 31.1 g (75%); m.p.=178–180° 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 it
  6. extractionis repeatedly extracted with ethyl acetate
  7. washwashed with water
  8. dry with materialdried with sodium sulphate
  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. customrecrystallised from toluene

Sources & evidence

ORD record
ord-b6fb007fed494e9fb18adb2beaab55d8
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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