반응 #1162555

반응 방정식

butyllithium

1-chloro-2-(2-methoxyethoxy)-ethane

9-(3,6-dioxaheptyl)-fluorene

1-chloro-2-(2-methoxyethoxy)-ethane

fluorene

butyllithium

→

9,9-bis(3,6-dioxaheptyl)-fluorene

용매

hexane

water

tetrahydrofuran

hexane

반응 조건

후처리

1. 1
   온도was cooled again to -40~-50° C
2. 2
   workup.STIRRINGThe mixture was subsequently stirred for 2 hours while the temperature
3. 3
   온도This solution was then cooled to -50° C.
4. 4
   workup.ADDITIONwas slowly added in 5 minutes under nitrogen protection
5. 5
   workup.STIRRINGThe mixture was stirred at -30 to -15° C. for 1 hour before it
6. 6
   온도was cooled again to 40 to -50° C
7. 7
   workup.STIRRINGThe mixture was subsequently stirred for 5 hours at 22° C.
8. 8
   추출extracted with ether
9. 9
   세척The etheral solution was washed with water and brine
10. 10
    건조dried with magnesium sulfate
11. 11
    기타evaporated
12. 12
    workup.DISTILLATIONThe residue was distilled
13. 13
    기타to collect 37.1 g (91%) of colorless liquid at 160° C./0.08 mm Hg

실험 절차

7.05 g of butyllithium dissolved in 44 ml of hexane was slowly added in 5 minutes into 18.28 g of fluorene dissolved in 150 ml of anhydrous tetrahydrofuran at -50° C. under nitrogen protection. The mixture was stirred at -30~15° C. for 1 hour before it was cooled again to -40~-50° C. Then, 15.23 g of 1-chloro-2-(2-methoxyethoxy)-ethane was added in 5 minutes. The mixture was subsequently stirred for 2 hours while the temperature was gradually increased to 22° C. The main product in the solution was 9-(3,6-dioxaheptyl)-fluorene as detected by GC-MS. This solution was then cooled to -50° C., and 7.1 g of butyllithium dissolved in 44 ml of hexane was slowly added in 5 minutes under nitrogen protection. The mixture was stirred at -30 to -15° C. for 1 hour before it was cooled again to 40 to -50° C. Then, 15.30 g of 1-chloro-2-(2-methoxyethoxy)-ethane was added during 5 minutes. The mixture was subsequently stirred for 5 hours at 22° C., dispersed in water, and extracted with ether. The etheral solution was washed with water and brine, dried with magnesium sulfate, and evaporated. The residue was distilled to collect 37.1 g (91%) of colorless liquid at 160° C./0.08 mm Hg. MS (m/z): 370 (M+), 219, 191, 178, 89, 59.

출처