Tetrabutylammonium Fluoride → HCID 86712673, compound

HRID 1779022Notes

Reaction equation

HRID 1779022 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]([F:39])([F:38])[C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[C:23]([C:32]#[C:33][Si](C)(C)C)[CH:22]=1>C1COCC1.CCOC(C)=O>[C:32]([C:23]1[CH:22]=[C:21]([C:20]([F:19])([F:39])[F:38])[CH:26]=[CH:25][C:24]=1[CH2:27][C:28]([O:30][CH3:31])=[O:29])#[CH:33]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86712672HCID 86712672, compound

Product 1

HCID 86712673HCID 86712673, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBAF (1.0 M in THF; 7.16 mL, 7.15 mmol) was added to a stirred solution of methyl 2-(4-(trifluoromethyl)-2-((trimethylsilyl)ethynyl)phenyl)acetate (A58) (1.50 g, 4.77 mmol) in THF (50 mL) at 0° C. After 5 minutes the resulting mixture was diluted with EtOAc (50 mL) then washed with 10% NaHCO3 (50 mL). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The residue was adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-10% EtOAc in petroleum benzine 40-60° C.) to give the title compound A59 as a dark red liquid (956 mg, 83%); 1H NMR (400 MHz, CDCl3) δ 7.77 (d, J=1.2 Hz, 1H), 7.57 (dd, J=8.1, 1.4 Hz, 1H), 7.43 (d, J=8.1 Hz, 1H), 3.90 (s, 2H), 3.72 (s, 3H), 3.36 (s, 1H). LCMS-A: rt 6.099 min; m/z 243.1 [M+H]+.

Workup

  1. washthen washed with 10% NaHCO3 (50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. custompurified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-10% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-6165e6cf927f47b885d147f1c1d71cd0
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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