Reaction #2006440

Reaction equation

n-butyllithium

methacryloyl chloride

sodium bicarbonate

1-cyclopentyl-1-cyclopentanol

→

title compound

Yield 91.0%

1-Cyclopentylcyclopentyl methacrylate

Yield 91.0%

Solvents

diethyl ether

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherTo a 1-L 3-necked round bottom flask equipped with a 250-mL pressure
2. 2
   workup.ADDITIONaddition funnel, a nitrogen inlet with thermocouple and an overhead stirrer
3. 3
   workup.ADDITIONwas then added slowly
4. 4
   Temperaturewith cooling over 1.5 hours
5. 5
   workup.ADDITIONwas carefully added
6. 6
   workup.STIRRINGThe mixture was stirred for 1 hour at which time it
7. 7
   Washthe organics washed with water, brine
8. 8
   Dryingdried for 1 hour over anhydrous magnesium sulfate
9. 9
   FiltrationFiltration and removal of the solvent at reduced pressure
10. 10
    Otherresulted in a light-colored oil which
11. 11
    Washwas eluted with hexane through a column of 600 g of silica gel
12. 12
    OtherThe UV active fractions were collected
13. 13
    Otherthe solvent removed at reduced pressure

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.

Source