Tetrabutylammonium Fluoride → HCID 67055507, compound

HRID 603982Notes

Reaction equation

HRID 603982 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C:21](=[O:78])[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][CH:75]([CH3:77])[CH3:76]>C1COCC1>[CH3:19][O:20][C:21](=[O:78])[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:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:32]=2[CH2:54][CH2:55][OH:56])=[CH:24][C:23]=1[O:74][CH:75]([CH3:76])[CH3:77]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67055459HCID 67055459, compound

Product 1

HCID 67055507HCID 67055507, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF) (0.29 mL, 0.29 mmol) was added to a solution of the silyl ether from step 3 (0.20 g, 0.24 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 0.10 g of 4-{2-[1-Benzhydryl-5-chloro-2-(2-hydroxy-ethyl)-1H-indol-3-yl]-ethoxy}-2-isopropoxy-benzoic acid methyl ester (brown solid) in 70% 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-3587a483208a44188a0b8ba0c53ee4be
Source dataset
uspto-grants-2011_03
Patent number
US07906548B2

Reaction notes

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