Cesium carbonate → Ethyl 3''-tert-butyl-4-[4-(tert-butyldimethylsilanyloxy)butoxy]-4''-diethylamino[1,1';3',1'']terphenyl-4-carboxylate

HRID 1158149Notes

Reaction equation

HRID 1158149 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][CH:24]=3)[CH:19]=[CH:20][C:21]=2O)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-:35].[Cs+].[Cs+].Br[CH2:41][CH2:42][CH2:43][CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47]>CN(C)C=O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH:17]=[C:18]([C:23]3[CH:24]=[CH:25][C:26]([O:35][CH2:41][CH2:42][CH2:43][CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:27][CH:28]=3)[CH:19]=[CH:20][CH:21]=2)[CH:8]=[CH:9][C:10]=1[N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 582370(4-Bromobutoxy)(tert-butyl)dimethylsilaneHCID 11676663Ethyl 3''-tert-butyl-4''-diethylamino-4'-hydroxy[1,1';3',1'']terphenyl-4-carboxylate

Product 1

HCID 86617895Ethyl 3''-tert-butyl-4-[4-(tert-butyldimethylsilanyloxy)butoxy]-4''-diethylamino[1,1';3',1'']terphenyl-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g of ethyl 3″-tert-butyl-4″-diethylamino-4′-hydroxy[1,1′;3′,1″]terphenyl-4-carboxylate obtained in Example 1d (2.2 mmol) are dissolved in 20 mL of dimethylformamide under a nitrogen atmosphere. 880 mg (2.7 mmol) of caesium carbonate are added. The reaction medium stirred at room temperature turns yellow. 0.64 mL of 1-bromo-4-(tert-butyldimethylsilanyloxy)butane (2.4 mmol) is then added and the reaction medium is heated at 80° C. for 18 hours. The reaction medium is then cooled to room temperature and then filtered. The solvents are evaporated off and the residue obtained is purified by chromatography on silica gel (eluent: 70/30 heptane/ethyl acetate).

Workup

  1. temperaturethe reaction medium is heated at 80° C. for 18 hours
  2. temperatureThe reaction medium is then cooled to room temperature
  3. filtrationfiltered
  4. customThe solvents are evaporated off
  5. customthe residue obtained
  6. customis purified by chromatography on silica gel (eluent: 70/30 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-47545cc8b4ff45eea1b76ee1fe4c10f6
Source dataset
uspto-grants-2010_10
Patent number
US07807708B2

Reaction notes

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