Methyl iodide → HCID 54284412, compound

HRID 1457958Notes

Reaction equation

HRID 1457958 reaction equation
O1CCC[CH2:2]1.[CH3:6][O:7][N:8]=[C:9]1[CH2:15][C:14]([CH3:17])([CH3:16])[CH:13]([OH:18])[CH:12]([N:19]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20](=[O:22])[CH3:21])[CH:11]=[C:10]1[CH3:30].[H-].[Na+].CI>C(O)(=O)C>[CH3:6][O:7][N:8]=[C:9]1[CH2:15][C:14]([CH3:16])([CH3:17])[CH:13]([O:18][CH3:2])[CH:12]([N:19]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20](=[O:22])[CH3:21])[CH:11]=[C:10]1[CH3:30]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 53639563HCID 53639563, compound

Product 1

HCID 54284412HCID 54284412, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of tetrahydrofuran (40 ml) containing the 4-(N-acetylbenzylamino)-5-hydroxy-2,6,6-trimethyl-2-cyclohepten-1-one methyloxime obtained in step 2 (9.5 g, 27.6 millimoles) there was gradually added 55% sodium hydride (3.6 g) while cooling on ice. After then adding methyl iodide (7.8 g, 55.2 millimoles) and stirring for 30 minutes, the mixture was returned to room temperature and stirring was continued for one hour. The reaction solution was poured into ice water (100 ml) containing acetic acid (1 ml), and subjected to extraction with benzene. After washing the benzene solution with water, it was dried over anhydrous magnesium sulfate. The benzene was distilled off, and the resulting residue was subjected to silica gel column chromatography with benzene-ethyl acetate (9:1) as the eluent, to obtain 8.51 g (86%) of 4-(N-acetylbenzylamino)-5-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one methyloxime as a colorless oil.

Workup

  1. temperaturewhile cooling on ice
  2. customwas returned to room temperature
  3. extractionsubjected to extraction with benzene
  4. washAfter washing the benzene solution with water, it
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationThe benzene was distilled off

Sources & evidence

ORD record
ord-fa3e5e6d524c46febf0c9b0670cdd085
Source dataset
uspto-grants-1998_12
Patent number
US05849801

Reaction notes

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