反応 #2006440

反応方程式

n-butyllithium

methacryloyl chloride

sodium bicarbonate

1-cyclopentyl-1-cyclopentanol

→

title compound

収率 91.0%

1-Cyclopentylcyclopentyl methacrylate

収率 91.0%

溶媒

diethyl ether

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他To 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
   温度with 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
   洗浄the organics washed with water, brine
8. 8
   乾燥dried for 1 hour over anhydrous magnesium sulfate
9. 9
   ろ過Filtration and removal of the solvent at reduced pressure
10. 10
    その他resulted in a light-colored oil which
11. 11
    洗浄was eluted with hexane through a column of 600 g of silica gel
12. 12
    その他The UV active fractions were collected
13. 13
    その他the solvent removed at reduced pressure

実験手順

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.

出典