Tetrabutylammonium Fluoride → HCID 67055507, compound

HRID 1821529Notes

Reaction equation

HRID 1821529 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-16e678f8a80e4aceb2da7ee14d484400
Source dataset
uspto-grants-2009_10
Patent number
US07605156B2

Reaction notes

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