반응 #349139

반응 방정식

1-(methoxymethyl)imidazole

butyllithium

4,4'-difluorobenzophenone

N,N,N',N'-tetramethylethylenediamine

→

α,α-Bis(p-fluorophenyl)-1-(methoxymethyl)imidazole-2-methanol

용매

water

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   기타The cooling means was then removed
3. 3
   workup.STIRRINGThe reaction mixture was stirred for 6 hours at room temperature
4. 4
   여과The precipitated lithium hydroxide was filtered off
5. 5
   농축the filtrate was concentrated
6. 6
   workup.DISTILLATIONby distilling off the solvents
7. 7
   workup.ADDITION2N Hydrochloric acid was added to the residue
8. 8
   추출after which the mixture was extracted with diethyl ether
9. 9
   기타The precipitate formed
10. 10
    여과was filtered off
11. 11
    세척washed with water
12. 12
    기타twice crystallised from a mixture of isopropyl alcohol and petroleum ether (boiling range 40°-60° C.)

실험 절차

To a solution of 11.2 g. (0.1 mol) of 1-(methoxymethyl)imidazole and 13.9 g. (0.12 mol) of N,N,N',N'-tetramethylethylenediamine in 150 ml. of anhydrous tetrahydrofuran 51 ml. (0.12 mol) of a butyllithium solution (20% in n-hexane) was added drop-wise over the course of one hour at -60° C., and under a nitrogen atmosphere. After the addition was completed, stirring was continued for another two hours. The cooling means was then removed and 25.1 g. (0.1 mol) of 4,4'-difluorobenzophenone in 150 ml. of anhydrous tetrahydrofuran were added drop-wise. The reaction mixture was stirred for 6 hours at room temperature and it was then decomposed with 15 ml. of water. The precipitated lithium hydroxide was filtered off and the filtrate was concentrated by distilling off the solvents. 2N Hydrochloric acid was added to the residue, after which the mixture was extracted with diethyl ether. The aqueous phase was made alkaline with 2N sodium hydroxide solution. The precipitate formed was filtered off, washed with water and twice crystallised from a mixture of isopropyl alcohol and petroleum ether (boiling range 40°-60° C.). α,α-Bis(p-fluorophenyl)-1-(methoxymethyl)imidazole-2-methanol was obtained. Melting point 133° C.

출처