o-Vanillin → 3-(2,6-Dimethoxy-phenyl)-2-[(E)-2-(2-hydroxy-3-methoxy-phenyl)-vinyl]-3H-quinazolin-4-one

HRID 1038936

反応式

HRID 1038936 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]1[CH3:22].[OH:23][C:24]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:25]=1[CH:26]=O>CC(O)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]1/[CH:22]=[CH:26]/[C:25]1[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:24]=1[OH:23]

参加物

4

反応物 2

HCID 8991o-Vanillin2 回HCID 6265293-(2,6-Dimethoxyphenyl)-2-methyl-4(3H)-quinazolinone

生成物 1

HCID 1360555383-(2,6-Dimethoxy-phenyl)-2-[(E)-2-(2-hydroxy-3-methoxy-phenyl)-vinyl]-3H-quinazolin-4-one収率 40%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 80 (170 mg, 0.57 mmol) and 2-hydroxy-3-methoxybenzaldehyde (9, 87 mg, 0.57 mmol) in AcOH (˜5 mL) was refluxed under N2 for 4 days and the reaction was monitored by MS and TLC. Additional 2-hydroxy-3-methoxybenzaldehyde (87 mg, 0.57 mmol) was added and the reaction mixture was refluxed for another 2 days. The solution was concentrated in vacuo and the crude product was purified by flash chromatography on silica gel eluting with EtOAc/hexanes to give the pure 81 as a yellow solid (98 mg, 40%). MS (APCI): m/z 431 (100%, [M+H]+).

後処理

  1. temperaturewas refluxed under N2 for 4 days
  2. temperaturethe reaction mixture was refluxed for another 2 days
  3. concentrationThe solution was concentrated in vacuo
  4. customthe crude product was purified by flash chromatography on silica gel eluting with EtOAc/hexanes

出典と根拠

ORDレコード
ord-dfd5fb0ff93c408ea87cee56a0e091a0
出典データセット
uspto-grants-2013_10
特許番号
US08552009B2

関連ノート

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