Ethyl bromoacetate → Ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylate

HRID 62798

Reaktionsgleichung

Reaktionsgleichung von HRID 62798
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[CH3:18]

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Produkt 1

HCID 4418640Ethyl 1-(2-ethoxy-2-oxoethyl)-2-oxocyclopentanecarboxylateAusbeute 37,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
56 °C

Versuchsvorschrift

To a solution of ethyl 2-oxocyclopentanecarboxylate (93.27 g, 597 mmol) and ethyl 2-bromoacetate (144.64 g, 866 mmol) in acetone (1.2 L) was added K2CO3 (165 g, 1194 mmol). The mixture was heated at 56° C. for 24 h. The solid was filtered off and the filter cake was washed with acetone (3×100 mL). The filtrate was concentrated and the resultant liquid was purified by a silica gel plug to give the title compound as light yellow liquid (54.7 g). LCMS m/z=243.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (t, J=7.14 Hz, 3H), 1.24 (t, J=7.14 Hz, 3H), 1.95-2.03 (m, 1H), 2.06-2.15 (m, 2H), 2.35-2.50 (m, 2H), 2.55-2.60 (m, 1H), 2.80 (dd, J=15.2, 2.09 Hz, 1H), 2.95 (dd, J=15.2, 2.09 Hz, 1H), 4.09 (q, J=7.14 Hz, 2H), 4.12 (q, J=7.14 Hz, 2H).

Aufarbeitung

  1. filtrationThe solid was filtered off
  2. washthe filter cake was washed with acetone (3×100 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe resultant liquid was purified by a silica gel plug

Quellen und Nachweise

ORD-Eintrag
ord-674f708676264ace99cd63176b38c8a3
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447041B2

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