Tetrabutylammonium Fluoride → HCID 67055505, compound

HRID 1821524Notes

Reaction equation

HRID 1821524 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C:21](=[O:76])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([Cl:40])[CH:38]=3)[N:33]([CH:41]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:32]=2[CH2:54][CH2:55][O:56][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:24][C:23]=1[O:74][CH3:75]>C1COCC1>[CH3:19][O:20][C:21](=[O:76])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([Cl:40])[CH:38]=3)[N:33]([CH:41]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:32]=2[CH2:54][CH2:55][OH:56])=[CH:24][C:23]=1[O:74][CH3:75]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67055483HCID 67055483, compound

Product 1

HCID 67055505HCID 67055505, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF) (0.37 mL, 0.37 mmol) was added to a solution of 4-(2-{1-Benzhydryl-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-chloro-1H-indol-3-yl}-ethoxy)-2-methoxy-benzoic acid methyl ester (0.25 g, 0.31 mmol) in THF (4 mL). Reaction was stirred at room temperature for 30 minutes. Reaction solution was concentrated by rotary evaporation and the resulting residue was purified with silica gel prep plates and 1:9 EtOAc/dichloromethane as eluent. Obtained 0.11 g of 4-{2-[1-Benzhydryl-5-chloro-2-(2-hydroxy-ethyl)-1H-indol-3-yl]-ethoxy}-2-methoxy-benzoic acid methyl ester (white solid) in 62% yield.

Workup

  1. customReaction
  2. customReaction solution
  3. concentrationwas concentrated by rotary evaporation
  4. customthe resulting residue was purified with silica gel prep plates and 1:9 EtOAc/dichloromethane as eluent

Sources & evidence

ORD record
ord-5ed02eee20c14b139461a2a957b25deb
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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