Acetic Acid → 3-Fluoro-2-vinyl-isonicotinic acid methyl ester

HRID 1426285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426285
[F:1][C:2]1[C:10]([CH:11]=[CH2:12])=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:13][Si](C=[N+]=[N-])(C)C.CCOCC.C(O)(=O)C>CO>[F:1][C:2]1[C:10]([CH:11]=[CH2:12])=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 696734763-Fluoro-2-vinylisonicotinic acid

Produkt 1

HCID 696727743-Fluoro-2-vinyl-isonicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-fluoro-2-vinylisonicotinic acid (1.3 g, 7.8 mmol, from Step 1) in methanol (20 mL) cooled to 0° C., was added dropwise 2.0M trimethylsilyldiazomethane in ether (21.6 mL, 44 mmol). When the reaction was complete, acetic acid was added dropwise to quench excess reagent and the volume of solvent was reduced in vacuo. The mixture was partitioned between saturated sodium bicarbonate solution and DCM. The aqueous portion was extracted with a total of three portions of DCM. The combined extracts were dried over sodium sulfate, decanted and concentrated and The product was used without further purification (1.4 g, 100%). 1H NMR (300 MHz, CDCl3): δ 8.47 (d, 1H), 7.62 (dd, 1H), 7.08 (ddd, 1H), 6.48 (dd, 1H), 5.65 (dd, 1H), 3.97 (s, 3H); LCMS (M+H)+: 182.0.

Aufarbeitung

  1. customto quench excess reagent
  2. customThe mixture was partitioned between saturated sodium bicarbonate solution and DCM
  3. extractionThe aqueous portion was extracted with a total of three portions of DCM
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. customThe product was used without further purification (1.4 g, 100%)

Quellen und Nachweise

ORD-Eintrag
ord-bfc661d6c6d44221bf7e79961084d0e6
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933085B2

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