Tetrabutylammonium Fluoride → HCID 58026130, compound

HRID 2387314Notes

Reaction equation

HRID 2387314 reaction equation
[CH3:1][C:2]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH2:22])=[O:21])([CH3:17])[CH2:3][C:4]([C:13]([F:16])([F:15])[F:14])([O:8][Si](C)(C)C)[CH2:5][C:6]#[CH:7].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[OH:8][C:4]([C:13]([F:14])([F:15])[F:16])([CH2:5][C:6]#[CH:7])[CH2:3][C:2]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH2:22])=[O:21])([CH3:1])[CH3:17]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58026145HCID 58026145, compound

Product 1

HCID 58026130HCID 58026130, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(1,1-dimethyl-3-trifluoromethyl-3-trimethylsilanyloxyhex-5-ynyl)benzamide (108 mg, 0.28 mmol) was treated with a 1M solution of TBAF in 3 mL of THF. The reaction mixture was stirred for 1 hour then diluted with 50 mL of ethyl acetate, washed with 25 mL of 1 M aqueous HCl, two 25 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude was purified by flash chromatography (12 g SiO2, hexanes to 1:1 hexanes:EtOAc) to give 2-(3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzamide as a white solid (82 mg, 93%). MS (ES+) m/z 314 [M+H]+.

Workup

  1. washwashed with 25 mL of 1 M aqueous HCl, two 25 mL portions of saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude was purified by flash chromatography (12 g SiO2, hexanes to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-b7adb4e6554d4310b8e5a6a1d4a9cf50
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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