Methyl iodide → HCID 21706269, compound

HRID 1594921Notes

Reaction equation

HRID 1594921 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].I[CH3:20]>C1COCC1>[CH3:20][C:5]1([CH:9]2[NH:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12665502HCID 12665502, compound

Product 1

HCID 21706269HCID 21706269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(3-Methoxyphenyl)-azepan-2-one, as described above in Step C, (0.13 g, 0.6 mmol) and NaH (60% dispersion in mineral oil) (0.03 g, 0.75 mmol) were dissolved in THF (5 mL) under Ar at ambient temperature. After 0.25 hours, iodomethane (0.064 mL, 1.0 mmol) was added and stirring was continued for 20 h. The reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL), the organic layer separated, washed with H2O, dried (MgSO4), filtered and concentrated to give the title compound after SiO2 chromatography (CHCl3:MeOH, 100:1 to 50:1).

Workup

  1. waitwas continued for 20 h
  2. customThe reaction mixture was partitioned between EtOAc (100 mL)—H2O (100 mL)
  3. customthe organic layer separated
  4. washwashed with H2O
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aaf4ccc0e3c8452784d6d35bff1438ff
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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