Hexane → HCID 58844048, compound

HRID 1919254Notes

Reaction equation

HRID 1919254 reaction equation
[CH2:1]([C:3]1([OH:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH3:10])[CH3:2].C([Li])CCC.CCCCCC.[C:23](Cl)(=[O:27])[C:24]([CH3:26])=[CH2:25]>CCOCC>[C:23]([O:11][C:3]1([CH2:1][CH3:2])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH3:10])(=[O:27])[C:24]([CH3:26])=[CH2:25]

Participants

6

Reactant 4

HCID 8058HexaneHCID 13528Methacryloyl chlorideHCID 66856532HCID 66856532, compoundHCID 178418339Butyllithium

Product 1

HCID 58844048HCID 58844048, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1-ethyl-2-methoxycyclohexanol from the previous step (10 g, 0.063 mole) in 50 ml ether was placed in a three neck flask equipped with a water condenser, addition funnel and a nitrogen inlet. This solution was cooled in an ice/water bath and n-butyllithium, 1.6 molar in hexane (45 ml, 0.072 mole) was added dropwise. The contents were allowed to warm to room temperature and stirred for 30 minutes. The mixture was cooled again in ice/water bath and methacryloyl chloride (7.31 g, 0.070 mole) in 25 ml ether was added dropwise and heated to reflux for 30 minutes. The reaction mixture was cooled to room temperature and quenched with 125 ml of deionized water. The organic phase was separated and the water phase was extracted with 50 ml ether. The combined ether solutions were washed with 100 ml brine and dried over anhydrous magnesium sulfate. The solvent was removed in a rotary evaporator and the crude product was chromatographed on a neutral alumina column using hexane as elutant. The product was a clear liquid (9.79 g) which was characterized by NMR and IR.

Workup

  1. customequipped with a water condenser, addition funnel and a nitrogen inlet
  2. temperatureThis solution was cooled in an ice/water bath
  3. temperatureheated
  4. temperatureto reflux for 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customquenched with 125 ml of deionized water
  7. customThe organic phase was separated
  8. extractionthe water phase was extracted with 50 ml ether
  9. washThe combined ether solutions were washed with 100 ml brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was removed in a rotary evaporator
  12. customthe crude product was chromatographed on a neutral alumina column

Sources & evidence

ORD record
ord-e3240a12305545aa8ba5190fb20db763
Source dataset
uspto-grants-2012_05
Patent number
US08168366B2

Reaction notes

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