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

HRID 1516634Notes

Reaction equation

HRID 1516634 reaction equation
[C:1]([CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=3)[CH:16]=[CH:17][C:18]=2[OH:19])=[CH:9][C:8]=1[C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:42][CH2:43][CH2:44][CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48]>CN(C)C=O>[C:1]([CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[C:15]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][CH:25]=3)[CH:16]=[CH:17][C:18]=2[O:19][CH2:42][CH2:43][CH2:44][CH2:45][O:46][Si:47]([C:50]([CH3:51])([CH3:53])[CH3:52])([CH3:48])[CH3:49])=[CH:9][C:8]=1[C:31]([CH3:33])([CH3:32])[CH3:34])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 582370(4-Bromobutoxy)(tert-butyl)dimethylsilaneHCID 86617903Ethyl 4''-(acetylethylamino)-3''-tert-butyl-4'-hydroxy[1,1';3',1'']terphenyl-4-carboxylate

Product 1

HCID 131728358Ethyl 4''-(acetylethylamino)-3''-tert-butyl-4'-[4-(tert-butyldimethylsilanyloxy)butoxy]-[1,1';3',1'']terphenyl-4-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to that of Example 2a, by reacting 260 mg of ethyl 4″-(acetylethylamino)-3″-tert-butyl-4′-hydroxy[1,1′;3′,1″]terphenyl-4-carboxylate (0.56 mmol) in 12 mL of dimethylformamide with 225 mg of caesium carbonate and 0.16 mL of 1-bromo-4-(tert-butyldimethylsilanyloxy)butane, 310 mg of ethyl 4″-(acetylethylamino)-3″-tert-butyl-4′-[4-(tert-butyldimethylsilanyloxy)butoxy]-[1,1′;3′,1″]terphenyl-4-carboxylate (yield=99%) are obtained in the form of an oil.

Sources & evidence

ORD record
ord-0c5358d062da437f9d5e69caf13e62dc
Source dataset
uspto-grants-2012_07
Patent number
US08227507B2

Reaction notes

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