1-Indanone → ethyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate

HRID 3398

Reaktionsgleichung

Reaktionsgleichung von HRID 3398
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C([Li])CCC.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C1COCC1>[C:17]([CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]1=[O:10])([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

5

Edukt 3

HCID 67351-IndanoneHCID 10928Ethyl chloroformateHCID 178418339Butyllithium

Produkt 1

HCID 10910629ethyl 1-oxo-2,3-dihydro-1H-indene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

1-Indanone (1.5 g, 11.36 mmols) was dissolved in dry THF in a three neck flask equipped with nitrogen inlet, septum and a guard tube. The flask was cooled to -20° C. for 10 minutes. Then butyl lithium (11.37 ml, 12.48 mmols) was added dropwise through the septum using the syringe. The reaction mixture was allowed to stand at -20° C. for 45 minutes and then ethyl chloroformate (1.08 ml, 10 mmols) was added dropwise using a syringe. The reaction mixture was stirred at -20° C. for 30 minutes and slowly brought to room temperature in about one hour. The reaction was worked-up by evaporating the THF and the product was chromatographed to yield 2-carbethoxy-1-indanone. NMR: (CDCl3):δ:1.25 (t, 3H, OCH2CH3); 3.45 (d, 2H, benzylic CH2); 3.65 (t, 1H, COCHCO); 4.2 (q, 2H, OCH2CH3); 7.4-7.5 (m, 4H, Ar-H).

Aufarbeitung

  1. customequipped with nitrogen inlet
  2. waitslowly brought to room temperature in about one hour
  3. customby evaporating the THF
  4. customthe product was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-234d9f67d5bc456d83ed16d8d4de410c
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733934

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