Methyl iodide → Methyl 9-methylxanthene-9-carboxylate

HRID 630425

Reaktionsgleichung

Reaktionsgleichung von HRID 630425
[CH:1]1[C:14]2[CH:13]([C:15]([O:17][CH3:18])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Li+].[CH3:20]C([N-]C(C)C)C.IC.[Cl-].[NH4+]>C1COCC1>[CH3:20][C:13]1([C:15]([O:17][CH3:18])=[O:16])[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 699662methyl 9H-xanthene-9-carboxylateHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 12068831Methyl 9-methylxanthene-9-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3.25 g (13.53 mmol) of methyl 9H-xanthene-9-carboxylate are dissolved in 70 ml THF, the solution is cooled with an ice bath and 10.15 ml (20.29 mmol) of a 2M solution of LDA are added drop wise whilst keeping the temperature at 0° C. After stirring at room temperature for 1 hr, 1.68 ml (27.06 mmol) of iodomethane are added drop wise and the system is stirred at rt overnight. The solution is poured over excess of saturated solution of ammonium chloride and is extracted thrice with ethyl ether. After washing with brine, the solution is dried and concentrated to give a reddish residue which is purified by column chromatography (Cl3CH/hexane from 1:3 to 1:1) to give 2.6 g of the title compound (75% yield) as a white solid.

Aufarbeitung

  1. temperaturethe solution is cooled with an ice bath
  2. customat 0° C
  3. stirringthe system is stirred at rt overnight
  4. extractionis extracted thrice with ethyl ether
  5. washAfter washing with brine
  6. customthe solution is dried
  7. concentrationconcentrated
  8. customto give a reddish residue which
  9. customis purified by column chromatography (Cl3CH/hexane from 1:3 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-489cca544c92488bb9474e4352f0fa2f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315463B2

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