Tetrabutylammonium Fluoride → Ethyl 4''-diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylate

HRID 1261529Notes

Reaction equation

HRID 1261529 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=2)=[CH:15][C:14]=1[C:30]1[CH:35]=[CH:34][C:33]([N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])=[C:32]([CH2:41][CH3:42])[CH:31]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:39]([N:36]([CH2:37][CH3:38])[C:33]1[CH:34]=[CH:35][C:30]([C:14]2[CH:15]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:23][CH:24]=3)[CH:17]=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9][OH:8])=[CH:31][C:32]=1[CH2:41][CH3:42])[CH3:40]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66672171Ethyl 4'-[3-(tert-butyldimethylsilanyloxy)propoxy]-4''-diethylamino-3''-ethyl[1,1';3',1'']terphenyl-4-carboxylate

Product 1

HCID 11662917Ethyl 4''-diethylamino-3''-ethyl-4'-(3-hydroxypropoxy)-[1,1';3',1'']terphenyl-4-carboxylateYield 53.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that of Example 2b, by reacting 660 mg of ethyl 4′-[3-(tert-butyldimethylsilanyloxy)propoxy]-4″-diethylamino-3″-ethyl[1,1′;3′,1″]terphenyl-4-carboxylate (1.1 mmol) in 25 mL of tetrahydrofuran with 1.2 mL of 1M tetrabutylammonium fluoride. 280 mg of ethyl 4″-diethylamino-3″-ethyl-4′-(3-hydroxypropoxy)-[1,1′;3′,1″]terphenyl-4-carboxylate are obtained (yield=52%).

Sources & evidence

ORD record
ord-d49d90b136ec4660bf94e8d84cdfbbf0
Source dataset
uspto-grants-2013_06
Patent number
US08470871B2

Reaction notes

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