Potassium Iodide → 6-Ethoxy-5-[3-(tetrahydro-pyran-2-yloxy)-propoxy]-indan-1-one

HRID 1714453

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[I-].[K+].[CH2:32](Br)[CH3:33]>CN(C=O)C.C(OCC)(=O)C>[CH2:32]([O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:12])=[CH:3][C:2]=1[O:1][CH2:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1)[CH3:33]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of 5,6-dihydroxy-indan-1-one (Intermediate O) (1.80 g, 0.01098 mole), potassium carbonate (3.80 g, 0.02744 mol), 2-(3-chloro-propoxy)-tetrahydro-pyran (Compound 18a) (1.37 g, 0.00769 mol) and potassium iodide (1.28 g, 0.00769 mol) in DMF (20 mL) was stirred at 60° C. for 4 hours. To this mixture was then added ethyl bromide (1.64 mL, 0.02196 mol) and continued to heat for further 4 h. The reaction mixture was then diluted with ethyl acetate, washed with water and dried over MgSO4. The solvent was removed in vacuo and the title compound was purified by silica gel column chromatography using 3:1 Hexanes:ethyl acetate as the eluent. MS m/z 334.2 (M+H)+;

Aufarbeitung

temperatureto heat for further 4 h
washwashed with water
dry with materialdried over MgSO4
customThe solvent was removed in vacuo
customthe title compound was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-5eb72317b1d04f09b06944c027c945c4
Quelldatensatz: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07795440B2

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