3-Phenoxyphenol → 4-Hydroxy-2-oxo-7-phenoxy-2H-chromene-3-carboxylic acid ethyl ester

HRID 2190909

Reaktionsgleichung

Reaktionsgleichung von HRID 2190909
[O:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18](=[O:30])[CH:19]([C:25](OCC)=[O:26])[C:20](OCC)=[O:21])[CH3:16].[Sn](Cl)(Cl)(Cl)Cl>>[CH2:15]([O:17][C:18]([C:19]1[C:20](=[O:21])[O:14][C:10]2[C:11]([C:25]=1[OH:26])=[CH:12][CH:13]=[C:8]([O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]=2)=[O:30])[CH3:16]

Komponenten

4

Edukt 3

HCID 128423-PhenoxyphenolHCID 24287Tin tetrachlorideHCID 80471Triethyl methanetricarboxylate

Produkt 1

HCID 866494634-Hydroxy-2-oxo-7-phenoxy-2H-chromene-3-carboxylic acid ethyl esterAusbeute 4,5 %

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

A mixture of 3-phenoxy-phenol (1.068 g, 5.73 mmol), 2-ethoxycarbonyl-malonic acid diethyl ester (3.65 mL, 17.2 mmol), and tin tetrachloride (14 μL, 0.11 mmol) was heated in a 200° C.-oil bath for 5 min; then cooled, the reaction mixture was directly purified on silica gel column chromatography (eluent: ethyl acetate in dichloromethane: 10% to 80%) to give the desired title product (84 mg, 4.4%). ESI (m/z): 327 (M+H)+.

Aufarbeitung

  1. temperaturethen cooled
  2. customthe reaction mixture was directly purified on silica gel column chromatography (eluent: ethyl acetate in dichloromethane: 10% to 80%)

Quellen und Nachweise

ORD-Eintrag
ord-f55ba2a4ea184d8a9cbba303f3198f6d
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324405B2

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