Methyl iodide → HCID 68870294, compound

HRID 1986394Notes

Reaction equation

HRID 1986394 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:28]I>C1COCC1>[CH3:28][CH:9]([CH2:8][CH2:7][N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 688741424-(4-Morpholinyl)-1-{3-[(phenylmethyl)oxy]phenyl}-1-butanone

Product 1

HCID 68870294HCID 68870294, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-morpholinyl)-1-{3-[(phenylmethyl)oxy]phenyl}-1-butanone (88 mg, 0.26 mmol) in THF (3 mL), was added NaH (23 mg, 60% suspension, 0.57 mmol). This suspension was stirred at rt for 30 min, then MeI (25 μl, 0.39 mmol) was added. The reaction mixture was stirred at rt for 3 h, then quenched with water. The reaction mixture was added EtOAC (100 ml), washed with brine, dried over Na2SO4, filtered and concentrated. The residue was then purified with flash chromatography (hexanes/ethyl acetate 1:2), to afford the title compound as a colorless oil (74 mg, 81%). MS (ES+) m/e 354 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 3 h
  2. customquenched with water
  3. additionThe reaction mixture was added EtOAC (100 ml)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was then purified with flash chromatography (hexanes/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-cbce27aa4d4c416f87205983432dbfab
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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