Potassium Hydroxide → 7-(trifluoromethoxy)-1H-indole

HRID 585843Notes

Reaction equation

HRID 585843 reaction equation
[OH-].[K+].C(OC(=O)[NH:7][C:8]1[C:13]([C:14]#[C:15][Si](C)(C)C)=[CH:12][CH:11]=[CH:10][C:9]=1[O:20][C:21]([F:24])([F:23])[F:22])C>C(O)(C)(C)C>[F:22][C:21]([F:24])([F:23])[O:20][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[NH:7][CH:15]=[CH:14]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59133031Carbamic acid, N-[2-(trifluoromethoxy)-6-[2-(trimethylsilyl)ethynyl]phenyl]-, ethyl ester

Product 1

HCID 223382447-(trifluoromethoxy)-1H-indoleYield 103.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

Potassium hydroxide (17.9 g, 321 mmol) was boiled for 2 h in t-butanol (500 mL). (2-Trifluoromethoxy-6-trimethylsilanylethynyl-phenyl)-carbamic acid ethyl ester (52.8 g, 153 mmol) dissolved in t-butanol (500 mL) was added and boiling was continued for 2 h. The solvent was removed in vacuo and the residue was partitioned between diethyl ether and water. The organic phases were washed with brine, pooled and dried with MgSO4. Evaporation of the solvent yielded 31.8 g of a brownish oil, which was purified by chromatography on silica gel with hexane/ethylacetate (9:1). This yielded the title compound, (30.2 g, 98%) as a yellow oil. (EI-MS: m/e=201.0 (M+))

Workup

  1. additionwas added
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between diethyl ether and water
  4. washThe organic phases were washed with brine
  5. dry with materialdried with MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2ce9054692f64d288038b59f80521fd6
Source dataset
uspto-grants-2005_08
Patent number
US06933387B2

Reaction notes

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