p-Toluenesulfonic acid → 2-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehyde

HRID 1161580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1161580
C[O:2][CH:3](OC)[C:4]1[C:5]([F:23])=[C:6]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[CH2:7][O:8][CH2:9][CH2:10][O:11]C1CCCCO1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1.O>[F:23][C:5]1[C:6]([CH2:7][O:8][CH2:9][CH2:10][OH:11])=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:4]=1[CH:3]=[O:2]

Komponenten

5

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 595174642-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran

Produkt 1

HCID 595168732-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehydeAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-[2-(3-Dimethoxymethyl-2-fluoro-5-methoxybenzyloxy]ethoxy]tetrahydropyran (1.035 g) was dissolved in 10 ml of THF and 3 ml of water, and 1 g of p-toluenesulfonic acid was added thereto. The resulting mixture was stirred at room temperature overnight, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate) to give the title compound (305 mg).

Aufarbeitung

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe desiccating agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-44c6ed68584a4ab982010c1ac8f88781
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816522B2

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