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

HRID 1930308Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930308
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9f691b33b9fd434fa712e9f15105e55d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188113B2

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