Acetic Acid → 1-Oxo-1-(2-oxocyclopentyl)propan-2-yl acetate

HRID 337008

Reaktionsgleichung

Reaktionsgleichung von HRID 337008
[C:1]([O:4][CH:5]([CH3:18])[C:6](=[O:17])[C:7]1[CH2:11][CH2:10][CH2:9][C:8]=1N1CCCC1)(=[O:3])[CH3:2].C(O)(=[O:21])C>O1CCCC1.O.ClCCl>[C:1]([O:4][CH:5]([CH3:18])[C:6](=[O:17])[CH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:21])(=[O:3])[CH3:2]

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 710141241-Oxo-1-(2-(pyrrolidin-1-yl)cyclopent-1-enyl)propan-2-yl acetate

Produkt 1

HCID 141483511-Oxo-1-(2-oxocyclopentyl)propan-2-yl acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Stir a mixture of 1-oxo-1-(2-(pyrrolidin-1-yl)cyclopent-1-enyl)propan-2-yl acetate (952.0 g), acetic acid (1500 mL) and water (1500 mL) in tetrahydrofuran (3000 mL) at room temperature for 2 days. Dilute the mixture with water (1200 mL) and dichloromethane (1200 mL). The organic layer is washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. Purify the residue by silica gel chromatograph (eluting with 3% to 10% ethyl acetate in petroleum ether) to give 1-oxo-1-(2-oxocyclopentyl)propan-2-yl acetate as oil (573.4 g, 2.89 mol, 72.6% for 2 steps).

Aufarbeitung

  1. washThe organic layer is washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurify the residue
  5. washby silica gel chromatograph (eluting with 3% to 10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-4eef28818fe4422a9cb044196349179c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889710B2

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