反応 #640554

反応方程式

9,10-bis(chloromethyl)anthracene

NaH

N-methylethanolamine

→

anthracene

収率 101.0%

溶媒

DMF

DMF

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   温度The resulting mixture was heated to −10° C. after a lapse of one hour
3. 3
   workup.ADDITIONfrom the completion of this addition
4. 4
   workup.STIRRINGstirred over one night
5. 5
   workup.DISTILLATIONwas distilled off under a reduced pressure
6. 6
   workup.DISSOLUTIONthe residue was dissolved in 200 ml of methylene chloride
7. 7
   ろ過insoluble matter was filtered out
8. 8
   workup.ADDITION50 ml of water was added to this, and TFA
9. 9
   workup.ADDITIONwas added
10. 10
    workup.STIRRINGwhile stirring until the pH of the solution
11. 11
    その他After leaving at rest for 15 minutes
12. 12
    その他the solution was separated into two layers
13. 13
    濃縮A water phase was concentrated
14. 14
    乾燥the water phase was freeze-dried

実験手順

That is, 2.06 g (27.0 mmol) of N-methylethanolamine was dissolved in 90 ml of anhydrous DMF in a 200 ml three-necked flask. Then, the resulting solution was cooled to −15° C. and to this, 1.08 g (27 mmol) of a 60% solution of NaH was added over 0.5 hours. After addition, the mixed solution was stirred at −15° C. for 1 hour. Then, 3.00 g (13.5 mmol) of 9,10-bis(chloromethyl)anthracene (1) was added gradually in a crystalline state. The resulting mixture was heated to −10° C. after a lapse of one hour from the completion of this addition and stirred over one night. After the completion of a reaction, DMF was distilled off under a reduced pressure, and the residue was dissolved in 200 ml of methylene chloride and insoluble matter was filtered out. 50 ml of water was added to this, and TFA was added while stirring until the pH of the solution becomes acid. After leaving at rest for 15 minutes, the solution was separated into two layers. A water phase was concentrated by repeating this operation two times and then the water phase was freeze-dried to obtain 2.43 g of quaternary anthracene salt 2 at a yield of 33%.

出典