Iodoethane → HCID 66707577, compound

HRID 1690855Notes

Reaction equation

HRID 1690855 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:17](I)[CH3:18].C1CCCCC1.C(OCC)(=O)C>CS(C)=O>[C:1]([O:5][C:6](=[O:14])[N:7]([CH2:17][CH3:18])[CH:8]1[CH2:13][CH2:12][CH:11]=[CH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11063381tert-Butyl cyclohex-3-en-1-ylcarbamateHCID 21867204Cyclohexane ethylacetate

Product 1

HCID 66707577HCID 66707577, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of cyclohex-3-enyl-carbamic acid tert-butyl ester (Kampferer, P.; Vasella, A. Helvetica Chimica Acta 2004, 87, 2764-2789) (4.34 g, 22 mmol) in 20 ml of DMSO was added sodium hydride (880 mg, 60% dispersion, 22 mmol) and after one hour of stirring ethyl iodide (1.78 ml, 22 mmol). After further stirring for 2 hours at room temperature the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and brine and extracted three times with ethyl acetate. The organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and after chromatography (silica, cyclohexane/ethyl acetate=12/1) the title compound (Rf=0.30, 2.88 g, 58% yield) was obtained as colorless solid.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe residue was diluted with water and brine
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-56b4ab63a7b241e488769b2fbdc4c686
Source dataset
uspto-grants-2012_04
Patent number
US08153689B2

Reaction notes

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