Pyridine → Acetic acid 2-allyl-4-fluorophenyl ester

HRID 1715566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715566
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:2]=[CH2:3].[C:12](OC(=O)C)(=[O:14])[CH3:13].N1C=CC=CC=1>O.CCOCC>[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[O:11][C:12](=[O:14])[CH3:13])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 113441122-Allyl-4-fluorophenol

Produkt 1

HCID 21443045Acetic acid 2-allyl-4-fluorophenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584184Diethylether waterLösungsmittel

Versuchsvorschrift

To crude (4p), acetic anhydride (36.5 mL, 386.4 mmol) and pyridine (37.5 mL, 463.7 mmol) were added. The resulting mixture was stirred at room temperature for 18 hours, checked by HPLC the next day (reaction appeared mostly complete). The mixture was then poured onto cold H2O/Et2O, the aqueous layer was extracted with Et2O (2×), the combined organic layers were washed sequentially with 10% HCl (3×), saturated NaHCO3 (2×), H2O (2×) and brine, and then dried over anhydrous Na2SO4. After concentration, crude product purity was checked by thin-layer chromatography (hexane/ethyl acetate, 7:3) and HPLC. No mass ion was observed. The crude product (5p) was carried on to next step directly without subsequent purification. 1HNMR (400 MHz, CDCl3) δ 7.04-6.91 (m, 3H), 6.09-5.65 (m, 1H), 5.19-5.06 (m, 2H), 3.27 (d, J=6.26 Hz, 2H), 2.30 (s, CH3).

Aufarbeitung

  1. customreaction
  2. extractionthe aqueous layer was extracted with Et2O (2×)
  3. washthe combined organic layers were washed sequentially with 10% HCl (3×), saturated NaHCO3 (2×), H2O (2×) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationAfter concentration, crude product purity
  6. customThe crude product (5p) was carried on to next step directly without subsequent purification

Quellen und Nachweise

ORD-Eintrag
ord-bb2464e66f4c4ec08fa7b885bb2f245d
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799782B2

Notizen zur Reaktion

Wird geladen…