Methyl iodide → HCID 66869064, compound

HRID 42979Notes

Reaction equation

HRID 42979 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[NH:5][CH:6]1[CH2:11][CH2:10][CH:9]=[C:8]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)[CH3:2].[H-].[Na+].[CH3:23]I>CN(C=O)C.C1COCC1>[CH2:1]([O:3][C:4](=[O:20])[N:5]([CH3:23])[CH:6]1[CH2:11][CH2:10][CH:9]=[C:8]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57459675HCID 57459675, compound

Product 1

HCID 66869064HCID 66869064, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

22 mg (0.082 mmol) (3-phenylethynyl-cyclohex-3-enyl)-carbamic acid ethyl ester are dissolved in 2 ml DMF and 1 THF. 8 mg (0.165 mmol) of a 60% dispersion of NaH in oil is added and the mixture stirred under argon for 90 minutes at room temperature. The reaction mixture is cooled to 0°, and 16 microliters MeI in 0.5 ml THF are added dropwise. After stirring one hour at room temperature, the reaction mixture is cooled to 0° again, ice is added and the crude product extracted with ethyl acetate, washed with water and saline, dried with sodium sulfate and column chromatographed using a 4:1 mixture of petroleum ether and ethyl acetate. Yield: 43%.

Workup

  1. temperatureThe reaction mixture is cooled to 0°
  2. stirringAfter stirring one hour at room temperature
  3. temperaturethe reaction mixture is cooled to 0° again
  4. additionice is added
  5. extractionthe crude product extracted with ethyl acetate
  6. washwashed with water and saline
  7. dry with materialdried with sodium sulfate and column
  8. customchromatographed
  9. additiona 4:1 mixture of petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-e9251103b5cb422a92b36adccb33d036
Source dataset
uspto-grants-2013_09
Patent number
US08536229B2

Reaction notes

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