Diethyl Ether → HCID 123165473, compound

HRID 2082208Notes

Reaction equation

HRID 2082208 reaction equation
[Mg].C(O[CH2:5][CH3:6])C.[CH:7]1[CH:12]=[CH:11][C:10]([N:13]([C:20]2[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH:8]=1.[CH2:27]([Si:31](Cl)(Cl)Cl)[CH2:28][CH2:29][CH3:30]>O>[C:14]1([N:13]([C:6]2[CH:5]=[CH:25][CH:20]=[CH:21][CH:22]=2)[C:10]2[CH:9]=[CH:8][C:7]([C:30]([C:17]3[CH:18]=[CH:19][C:14]([N:13]([C:10]4[CH:9]=[CH:8][CH:7]=[CH:12][CH:11]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:16]=3)([C:23]3[CH:24]=[CH:25][C:20]([N:13]([C:10]4[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=4)[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:21][CH:22]=3)[CH2:29][CH2:28][CH2:27][SiH3:31])=[CH:12][CH:11]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 3283Diethyl Ether4×HCID 24142Silane, butyltrichloro-HCID 6428384-BromotriphenylamineHCID 5462224Magnesium

Product 1

HCID 123165473HCID 123165473, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.6 g (24.9 mmol) of metallic magnesium was placed in a 200-ml four-necked flask equipped with a mechanical stirrer, a condenser, a nitrogen-inlet tube and a dropping funnel, and the inside atmosphere was replaced with nitrogen. 100 ml of diethyl ether was added and stirring was initiated. To this solution, 20 ml of a diethyl ether solution of 6.5 g (20 mmol) of 4-bromotriphenylamine was gradually added dropwise. When about 5 ml was added, mild reflux began. Under reflux conditions, the remainder of the diethyl ether solution was added. After completion of the addition, reflux was continued for 1 more hour. The Gringnard solution thus obtained was cooled to room temperature, and then 20 ml of a diethyl ether solution of 1.3 g (6.6 mmol) of n-butyltrichlorosilane was gradually added dropwise under reflux conditions. After completion of the addition, the reaction mixture was stirred under reflux conditions for 2 hours. Then, the mixture was cooled on ice water bath, and ice cooling conditions, 50 ml of water was added for hydrolysis. The ether layer was extracted and washed with a saturated aqueous solution of sodium hydrogen carbonate and then with two portions of water, followed by drying with anhydrous sodium sulfate. After drying, the diethyl ether was distilled off to yield a white solid, which was then recrystallized with n-hexane/toluene (1/1) to yield 3.7 g of the desired product (yield 68%).

Workup

  1. customequipped with a mechanical stirrer, a condenser, a nitrogen-inlet tube and a dropping funnel
  2. additionWhen about 5 ml was added
  3. temperaturemild reflux
  4. additionAfter completion of the addition
  5. temperaturereflux
  6. customThe Gringnard solution thus obtained
  7. additionAfter completion of the addition
  8. stirringthe reaction mixture was stirred under reflux conditions for 2 hours
  9. temperatureThen, the mixture was cooled on ice water bath
  10. extractionThe ether layer was extracted
  11. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  12. dry with materialby drying with anhydrous sodium sulfate
  13. customAfter drying
  14. distillationthe diethyl ether was distilled off
  15. customto yield a white solid, which
  16. customwas then recrystallized with n-hexane/toluene (1/1)

Sources & evidence

ORD record
ord-8b20f7006c3e494ba464afe8298a3374
Source dataset
uspto-grants-1993_02
Patent number
US05187310

Reaction notes

Loading…