Methacryloyl chloride → HCID 21131313, compound

HRID 1919258Notes

Reaction equation

HRID 1919258 reaction equation
[CH:1]1([C:6]2([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)C>[C:17]([O:11][C:6]1([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:7][CH2:8][CH2:9][CH2:10]1)(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

7

Reactant 4

HCID 13528Methacryloyl chlorideHCID 516892Sodium BicarbonateHCID 43809304HCID 43809304, compoundHCID 178418339Butyllithium

Product 1

HCID 21131313HCID 21131313, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a 1-L 3-necked round bottom flask equipped with a 250-mL pressure equalizing addition funnel, a nitrogen inlet with thermocouple and an overhead stirrer was added 56 g (0.364 mol) of 1-cyclopentyl-1-cyclopentanol and 400 mL of anhydrous tetrahydrofuran. The addition funnel was charged with 250 mL (0.4 mol) of n-butyllithium (1.6M in hexane) which was then added to the cooled alcohol over 2 hours. The addition funnel was then charged with a solution of 41 g (0.39 mol) of freshly distilled methacryloyl chloride in 100 mL of dry tetrahydrofuran which was then added slowly with cooling over 1.5 hours. The reaction mixture was allowed to warm to room temperature with stirring overnight after which 100 mL of saturated sodium bicarbonate was carefully added with stirring. The mixture was stirred for 1 hour at which time it was diluted with 1 L of diethyl ether and the organics washed with water, brine and dried for 1 hour over anhydrous magnesium sulfate. Filtration and removal of the solvent at reduced pressure resulted in a light-colored oil which was eluted with hexane through a column of 600 g of silica gel. The UV active fractions were collected and the solvent removed at reduced pressure to yield 74 g (91%) of the title compound as a clear, colorless oil.

Workup

  1. customTo a 1-L 3-necked round bottom flask equipped with a 250-mL pressure
  2. additionaddition funnel, a nitrogen inlet with thermocouple and an overhead stirrer
  3. additionwas then added slowly
  4. temperaturewith cooling over 1.5 hours
  5. additionwas carefully added
  6. stirringThe mixture was stirred for 1 hour at which time it
  7. washthe organics washed with water, brine
  8. dry with materialdried for 1 hour over anhydrous magnesium sulfate
  9. filtrationFiltration and removal of the solvent at reduced pressure
  10. customresulted in a light-colored oil which
  11. washwas eluted with hexane through a column of 600 g of silica gel
  12. customThe UV active fractions were collected
  13. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-bfa0d50a9d7d44b08360ddf22599e87f
Source dataset
uspto-grants-2012_05
Patent number
US08168366B2

Reaction notes

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