Methyl iodide → methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

HRID 22190

Reaktionsgleichung

Reaktionsgleichung von HRID 22190
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH3:12][O:13][C:14](=O)[O:15]C.[H-].[Na+].[CH3:20]I>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6]([CH3:20])([C:14]([O:13][CH3:12])=[O:15])[CH2:5]2

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 1425995-Chloro-1-indanone

Produkt 1

HCID 19384693methyl 5-chloro-2,3-dihydro-2-mehtyl-1-oxo-1H-indene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 8.0 g of 5-chloroindanone and 4.2 ml of dimethylcarbonate in 60 ml of THF was added 4.0 g of 60% NaH and the mixture was heated to reflux under N2 overnight. After this time the reaction was cooled to room temperature and 4.0 ml of methyl iodide was added and the mixture was reheated to reflux overnight. The reaction was then cooled and partitioned between ether and 5% aqueous NaHCO3 and the aqueous extracts were washed twice with ether. The combined aqueous extracts were dried over MgSO4 and concentrated to 11.24 g of a brown oil. Chromatogrpahy on silica gel (10% ethyl acetate/hexane) afforded 4.25 g of the title compound as a brown oil. 1H NMR (CDCl3) δ 1.52 (s, 3H), 2.96 (d, 1H), 3.68 (s, 3H), 3.69 (d, 1H), 7.40 (d, 1H), 7.47 (s, 1H), 7.71 (d, 1H).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux under N2 overnight
  3. temperatureto reflux overnight
  4. temperatureThe reaction was then cooled
  5. custompartitioned between ether and 5% aqueous NaHCO3
  6. washthe aqueous extracts were washed twice with ether
  7. dry with materialThe combined aqueous extracts were dried over MgSO4
  8. concentrationconcentrated to 11.24 g of a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-419a3f8533f6491a8575202ffbe54415
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428027

Verknüpfte Notizen

Wird geladen…