Water → 4-[4-Sulfonylpyranoyloxy]-2-methoxybenzoic acid

HRID 1698

Reaktionsgleichung

Reaktionsgleichung von HRID 1698
[S:1](=[C:4]1[CH:9]=[CH:8][O:7][C:6]([C:10]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[C:15]([O:23][CH3:24])[CH:14]=2)=[O:11])=[CH:5]1)(=[O:3])=[O:2].O.O[Li].O>C1COCC1>[S:1](=[C:4]1[CH:9]=[CH:8][O:7][C:6]([C:10]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:23][CH3:24])[CH:14]=2)=[O:11])=[CH:5]1)(=[O:2])=[O:3]

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86752226Methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate

Produkt 1

HCID 867522274-[4-Sulfonylpyranoyloxy]-2-methoxybenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a stirred solution of methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate (470 mg, 1.5 mmol)in THF:H2O (18 mL: 2 mL) was added LiOH.H2O (128 mg, 3 mmol). The reaction was heated to 45° C. over 12 h and then cooled to ambient temperature. The solvent was removed under reduced pressure. The crude solid passed through a plug of silca gel packed in 80:20 hexanes:EtOAc and eluted with same. The solvent was removed under reduced pressure to afford 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoic acid as a white solid.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. customThe solvent was removed under reduced pressure
  3. washEtOAc and eluted with same
  4. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-633f98fd12d84e92930ec5dccc1d3957
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726172

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