Ethyl Acetate → HCID 86712711, compound

HRID 1779069Notes

Reaction equation

HRID 1779069 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]([F:39])([F:38])[C:21]1[CH:22]=[CH:23][C:24]([C:32]#[C:33][Si](C)(C)C)=[C:25]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:26]=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1>[C:32]([C:24]1[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:39])[F:38])=[CH:26][C:25]=1[CH2:27][C:28]([O:30][CH3:31])=[O:29])#[CH:33]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 86712709HCID 86712709, compound

Product 1

HCID 86712711HCID 86712711, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1.0 M in THF; 4.29 mL, 4.29 mmol) was added to a solution of methyl 2-(5-(trifluoromethyl)-2-((trimethylsilyl)ethynyl)phenyl)acetate (A104) (0.900 g, 2.86 mmol) in THF (25 mL) at 0° C. The resulting mixture was stirred at 0° C. for 5 minutes before the addition of EtOAc (50 mL) and 10% aqueous NaHCO3 (50 mL). The layers were separated and the organic phase dried (MgSO4) then the solvent was evaporated under reduced pressure. The residue was adsorbed onto silica gel and purified by silica gel column chromatography (Biotage Isolera, SiO2 cartridge, 0-10% EtOAc in petroleum benzine 40-60° C.) to give the title compound A105 as a light brown coloured liquid (0.498 g, 72%); 1H NMR (400 MHz, CDCl3) δ 7.60 (d, J=8.1 Hz, 1H), 7.56 (s, 1H), 7.50 (d, J=8.1 Hz, 1H), 3.89 (s, 2H), 3.71 (s, 3H), 3.40 (s, 1H). LCMS-A: rt 6.094 min; m/z 243.1 [M+H]+.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic phase dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. custompurified by silica gel column chromatography (Biotage Isolera, SiO2 cartridge, 0-10% EtOAc in petroleum benzine 40-60° C.)

Sources & evidence

ORD record
ord-d2c0570d674a4fa7967159dce1680723
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

Loading…