Diethyl Ether → tert-Butyl 3-oxocyclopentane-1-carboxylate

HRID 1367494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367494
[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[C:10](O)([CH3:13])([CH3:12])[CH3:11].C(OCC)C>CN(C)C1C=CN=CC=1.ClCCl>[C:10]([O:8][C:7]([CH:4]1[CH2:5][CH2:6][C:2](=[O:1])[CH2:3]1)=[O:9])([CH3:13])([CH3:12])[CH3:11]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 6386tert-ButanolHCID 2277983-Oxocyclopentanecarboxylic acid

Produkt 1

HCID 14009986tert-Butyl 3-oxocyclopentane-1-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
2 °C

Versuchsvorschrift

To a cold (ice bath) solution of 3-oxo-1-cyclopentanecarboxylic acid (1.50 g), tert-butylalcohol (1.05 g) and 4-dimethylaminopyridine (140 mg) in dichloromethane (9 mL) was added a solution of dicyclocarbodiimide in dichloromethane (9 mL). The mixture was stirred 3 hours at ca. 2° C. then diethylether (30 mL) was added and the precipitate was filtered off and discarded. The solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (9:1 v/v) as eluant to afford the title compound (1.80 g, 96%) as colorless oil. MS (EI): 111 (M-OtBu.)+.

Aufarbeitung

  1. filtrationthe precipitate was filtered off
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (9:1 v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-cd421189375b431ca283a94321e025c6
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893099B2

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