Potassium Carbonate → Ethyl 2-(2-ethynyl-4-fluoro-5-nitrophenyl)acetic acid

HRID 1930308Notes

Reaction equation

HRID 1930308 reaction equation
[F:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12]([O:14]CC)=[O:13])=[C:4]([C:17]#[C:18][Si](C)(C)C)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:29]1COC[CH2:30]1.CO>CCOCC>[CH2:29]([CH:11]([C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([F:1])=[CH:3][C:4]=1[C:17]#[CH:18])[C:12]([OH:14])=[O:13])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21899815MeOH tetrahydrofuranHCID 69088386Ethyl 2-(4-fluoro-5-nitro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate

Product 1

HCID 86620161Ethyl 2-(2-ethynyl-4-fluoro-5-nitrophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-(4-fluoro-5-nitro-2-(2-(trimethylsilyl)ethynyl)phenyl)acetate (0.85 g, 2.6 mmol) and K2CO3 (3.6 g) were dissolved in THF/MeOH (5:1, 30 mL) and the mixture was stirred overnight at RT. The reaction mixture was diluted with Et2O and washed with sat'd NH4Cl solution. The organic layer was dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel column chromatography to obtain ethyl 2-(2-ethynyl-4-fluoro-5-nitrophenyl)acetic acid.

Workup

  1. washwashed with sat'd NH4Cl solution
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f691b33b9fd434fa712e9f15105e55d
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…