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

HRID 853077Notes

Reaction equation

HRID 853077 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-be1c40840710462a92d5ba8d004d170d
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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