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

HRID 2190909

반응식

HRID 2190909 반응식
[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]

참가 물질

4

반응물 3

HCID 128423-PhenoxyphenolHCID 24287Tin tetrachlorideHCID 80471Triethyl methanetricarboxylate

생성물 1

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

반응 조건

온도
200 °C

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-f55ba2a4ea184d8a9cbba303f3198f6d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324405B2

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