Methyl iodide → Methyl-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-carbamic acid tert-butyl ester

HRID 751232Notes

Reaction equation

HRID 751232 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].I[CH3:24].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[N:7]([CH3:24])[CH2:8][C:9]#[C:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]([F:20])([F:21])[F:19])=[CH:15][CH:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68823297[3-(4-Trifluoromethoxy-phenyl)-prop-2-ynyl]-carbamic acid tert-butyl ester

Product 1

HCID 68824454Methyl-[3-(4-trifluoromethoxy-phenyl)-prop-2-ynyl]-carbamic acid tert-butyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[3-(4-Trifluoromethoxy-phenyl)-prop-2-ynyl]-carbamic acid tert-butyl ester (500 mg, 1.6 mmol) was added to an ice cold solution of iodomethane (100 μl, 1.7 mmol) and sodium hydride (73 mg, 1.7 mmol; 55% suspension in mineral oil) in DMF (5 ml). The reaction mixture was stirred for 5 h at ambient temperature, cooled to 0° C. and carefully quenched with saturated aqueous ammonium chloride solution. Ice water/ethyl acetate 1/1 were added, the layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined extracts were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica gel, heptane/AcOEt) to give 258 mg (0.8 mmol, 49%) of the title compound as yellow oil.

Workup

  1. temperaturecooled to 0° C.
  2. customcarefully quenched with saturated aqueous ammonium chloride solution
  3. additionIce water/ethyl acetate 1/1 were added
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted two times with ethyl acetate
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by flash chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-056b1c4f1bfd4bec8b704fdc0d0f432b
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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