Methanol → 4-t-Butoxy-2,3,6-trifluoro-5-methoxypyridine

HRID 1875

Reaktionsgleichung

Reaktionsgleichung von HRID 1875
[C:1]([O:5][C:6]1[C:11]([OH:12])=[C:10]([F:13])[N:9]=[C:8]([F:14])[C:7]=1[F:15])([CH3:4])([CH3:3])[CH3:2].[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6]1[C:11]([O:12][CH3:16])=[C:10]([F:13])[N:9]=[C:8]([F:14])[C:7]=1[F:15])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 106565874-t-Butoxy-2,3,6-trifluoro-5-hydroxypyridine

Produkt 1

HCID 104899104-t-Butoxy-2,3,6-trifluoro-5-methoxypyridineAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 237 mg (1.07 mmol) of 4-t-butoxy-2,3,6-trifluoro-5-hydroxypyridine, from step 275a above, in 3 mL of anhydrous THF was added 335 mg (1.277 mmol) of triphenyl phosphine and 0.060 mL (1.48 mmol) of methanol. To this solution was added 0.200 mL (1.270 mmol) of DEAD dropwise at room temperature. The reaction was complete in 10 min, so the solvents were removed under vacuum and the residue was purified by flash chromatography on silica gel, eluting with 1:16 ethyl acetate:hexane to give 215.6 mg of the title product as a colorless liquid after removal of the solvent.

Aufarbeitung

  1. customwere removed under vacuum
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with 1:16 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-60ba32da8a3a420db576adcfd7bcef8c
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726182

Verknüpfte Notizen

Wird geladen…