Dimethylformamide → 2,3,6,7,10,11-Hexakis[2-(2-methoxyethoxy)ethoxy]triphenylene

HRID 991377Notes

Reaction equation

HRID 991377 reaction equation
CN(C)[CH:3]=[O:4].[H-].[Na+].[OH:8][C:9]1[C:26]([OH:27])=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][C:20]([OH:29])=[C:21]([OH:28])[CH:22]=3)[C:17]3[C:12](=[CH:13][C:14]([OH:31])=[C:15]([OH:30])[CH:16]=3)[C:11]=2[CH:10]=1.C1(C)C=CC(S(OO[CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])(=O)=O)=CC=1>C(Cl)(Cl)Cl.O>[O:8]([C:9]1[C:26]([O:27][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])=[CH:25][C:24]2[C:23]3[C:18](=[CH:19][C:20]([O:29][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])=[C:21]([O:28][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])[CH:22]=3)[C:17]3[C:12](=[CH:13][C:14]([O:31][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:4][CH3:3])=[C:15]([O:30][CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49])[CH:16]=3)[C:11]=2[CH:10]=1)[CH2:43][CH2:44][O:45][CH2:46][CH2:47][O:48][CH3:49]

Participants

7

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 110886102,3,6,7,10,11-HexahydroxytriphenyleneHCID 184135022-(2-Methoxyethoxy)ethoxy tosylate

Product 1

HCID 152191092,3,6,7,10,11-Hexakis[2-(2-methoxyethoxy)ethoxy]triphenyleneYield 5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

In a reaction vessel, 15 ml of dry N,N-dimethylformamide (DMF) and 0.77 g (19.3 mM) of NaH (60 W in mineral oil) were placed. Then, 0.92 g (2.84 mM) of 2,3,6,7,10,11-hexahydroxytriphenylene was added thereto on a water bath, and after 1 hour of stirring, a mixture liquid of 6.4 g (23.3 mM of 1,4,7-trioxaoctyl p-toluenesulfonate and 5 ml of dry DMF was added dropwise thereto, followed by 5 hours of stirring at 80° C. After the reaction, water was added to the reaction mixture, followed by extraction two times with toluene. The extract was washed with water and dried with anhydrous sodium sulfate, followed by distilling-off the solvent and purification three times by silica gel column chromatography (eluent: chloroform to obtain 0.14 g (0.15 mM) of 2,3,6,7,10,11-hexa(1,4,7-trioxaoctyl)triphenylene (Yield: 5%), which showed a melting point of 54 ° C.

Workup

  1. waitfollowed by 5 hours
  2. stirringof stirring at 80° C
  3. additionwas added to the reaction mixture
  4. extractionfollowed by extraction two times with toluene
  5. washThe extract was washed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. distillationfollowed by distilling-off the solvent and purification three times by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-3035550a02f349e384590817d6bb760b
Source dataset
uspto-grants-2002_10
Patent number
US06464904B1

Reaction notes

Loading…