Ethylene Glycol → 3-Methoxy-8-(2-methyl-[1,3]-dioxolan-2-yl)-benzo[c]chromen-6-one

HRID 987591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987591
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[O:10][C:9](=[O:19])[C:8]=2[CH:20]=1)(=[O:3])[CH3:2].[CH2:21](O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:18][O:17][C:13]1[CH:12]=[C:11]2[C:16]([C:7]3[CH:6]=[CH:5][C:4]([C:1]4([CH3:2])[O:23][CH2:22][CH2:21][O:3]4)=[CH:20][C:8]=3[C:9](=[O:19])[O:10]2)=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 103332378-Acetyl-3-methoxy-benzo[c]chromen-6-one

Produkt 1

HCID 113244043-Methoxy-8-(2-methyl-[1,3]-dioxolan-2-yl)-benzo[c]chromen-6-oneAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

The compound from Step E (5.2 g, 19 mmol), ethylene glycol (4.4 g, 71 mmol) and a catalytic amount of p-toluenesulfonic acid (0.2 g) were dissolved in benzene (300 mL) and refluxed for 28 h. The solvent was removed and the crude product chromatographed on silica gel with hexane/ethyl acetate (2:1) to yield 3.6 g (60%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 1.75 (3H, s, CH3), 3.82 (2H, t, OCH2), 3.91 (3H, s, OCH3), 4.10 (2H, t, OCH2), 6.93 (1H, s, ArH), 6.98 (1H, d, ArH), 7.47 (3H, m, ArH), 8.04 (1H, s, ArH).

Aufarbeitung

  1. temperaturerefluxed for 28 h
  2. customThe solvent was removed
  3. customthe crude product chromatographed on silica gel with hexane/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f55f89b8a0c14e0092ec97927e0a6b0e
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06632835B2

Notizen zur Reaktion

Wird geladen…