Hydrochloric Acid → L 748780

HRID 1648354Notes

Reaction equation

HRID 1648354 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:31])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]([C:19](=[O:29])[C:20]2[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=2[Cl:28])[C:9]=1[CH3:30].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-].Cl>C1COCC1>[Cl:28][C:21]1[CH:22]=[C:23]([Cl:27])[CH:24]=[C:25]([Cl:26])[C:20]=1[C:19]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[C:8]([CH2:7][C:6]([OH:31])=[O:5])=[C:9]1[CH3:30])=[O:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 15292265HCID 15292265, compound

Product 1

HCID 127942L 748780Yield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(2,4,6-trichlorobenzoyl)-5-methoxy-2-methyl-3-indolyl acetic acid 2-(trimethylsilyl)ethyl ester (2.80 g) in THF (25.0 mL) at 0° C. was added TBAF (14.7 mL). After a period of 5 h at room temperature, the reaction mixture was acidified by the addition of NH4Cl and HCl, extracted with EtOAc, dried over Na2SO4 and evaporated. The resulting solid was washed with 10% EtOAc in hexane and recrystallized (EtOAc-hexane) to afford 1.73 g of the title compound, m.p. 193°-196° C.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. washThe resulting solid was washed with 10% EtOAc in hexane
  5. customrecrystallized (EtOAc-hexane)

Sources & evidence

ORD record
ord-dd6b41a17d2048dbbc8f93938046312e
Source dataset
uspto-grants-1995_07
Patent number
US05436265

Reaction notes

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