Acetic Anhydride → (+)-Acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl ester

HRID 2393900

Reaktionsgleichung

Reaktionsgleichung von HRID 2393900
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:12][C@H:11]([OH:13])[CH:10]=[CH:9]1.[C:14](OC(=O)C)(=[O:16])[CH3:15].CN(C1C=CC=CN=1)C.C(OCC)(=O)C>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:12][C@H:11]([O:13][C:14](=[O:16])[CH3:15])[CH:10]=[CH:9]1

Komponenten

6

Edukt 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 13623252cis-4-Tetrahydropyranyloxy 2-cyclopentenol

Produkt 1

HCID 13623284(+)-Acetic acid cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enyl esterAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Dissolve (-)-cis-4-(tetrahydro-pyran-2-yloxy)-cyclopent-2-enol (292 mg, 1.59 mmol, prepared in example 11) in pyridine (2.8 mL) and treat with acetic anhydride (0.39 mL) and dimethylaminopyridine (16 mg). Stir the reaction overnight. Concentrate the reaction under vacuum, dissolve the residue with ethyl acetate (10 mL). Wash with 0.5M hydrochloric acid that is 1/2 saturated with brine (2×10 mL), saturated sodium bicarbonate (10 mL), brine (10 mL), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by chromatography (silica gel, 10 g, 1.5×4 cm column, 20% ethyl acetate/hexane) to provide the title compound (290 mg, 81%).

Aufarbeitung

  1. customthe reaction overnight
  2. concentrationConcentrate
  3. customthe reaction under vacuum
  4. washWash with 0.5M hydrochloric acid that
  5. dry with materialdry over anhydrous magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by chromatography (silica gel, 10 g, 1.5×4 cm column, 20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c5bc7356e886403180c45fec4b7b4668
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05808112

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