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

HRID 2190909

反応式

HRID 2190909 の反応式
[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]

参加物

4

反応物 3

HCID 128423-PhenoxyphenolHCID 24287Tin tetrachlorideHCID 80471Triethyl methanetricarboxylate

生成物 1

HCID 866494634-Hydroxy-2-oxo-7-phenoxy-2H-chromene-3-carboxylic acid ethyl ester収率 4.5%

反応条件

温度
200 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-f55ba2a4ea184d8a9cbba303f3198f6d
出典データセット
uspto-grants-2012_12
特許番号
US08324405B2

関連ノート

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