Dimethylformamide → HCID 66869064, compound

HRID 1394233Notes

Reaction equation

HRID 1394233 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]N(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

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 57459675HCID 57459675, compound

Product 1

HCID 66869064HCID 66869064, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

22 mg (0.082 mmol) (3-phenylethynyl-cyclohex-3-enyl)-carbamic acid ethyl ester are dissolved in 2 ml DMF and 1 mL 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 Mel in 0.5 ml THF are added dropwise. After stirring one hour at room tenmperature, 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 tenmperature
  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-d03321c5905643cbb31f16c520499c15
Source dataset
uspto-grants-2008_03
Patent number
US07348353B2

Reaction notes

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