反応式
CN(C)[CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[C:9]([O:17][CH3:18])[CH:8]=1)=[O:6].[OH:20][C:21]1[C:28]([OH:29])=[C:27]([O:30][CH3:31])[CH:26]=[CH:25][C:22]=1C=O.[CH3:32]CN(CC)CC>[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[CH3:18][O:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH3:14])[C:10]=1[O:15][CH3:16])[C:5]([C:4]1[CH2:31][O:30][C:27]2[C:26]([CH:3]=1)=[CH:25][CH:22]=[C:21]([O:20][CH3:32])[C:28]=2[OH:29])=[O:6]参加物
5
反応物 3
生成物 1
試薬・触媒・溶媒 1
反応条件
- 温度
- 115 °C
実験手順
A mixture of 2-(N,N-dimethylamino)ethyl-(3′,4′,5′-trimethoxyphenyl)ketone (4, 1.17 g, 4.37 mmol), 2,3-dihydroxy-4-methoxybenzaldehyde (2, 0.74 g, 4.37 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (0.12 g, 0.44 mmol) and Et3N (1 ml) was heated under reflux at 115° C. for 3.5 hours. After quenching with 1M HCl, the product was extracted with CH2Cl2. The combined extract was washed with water, rinsed with brine and dried over anhydrous magnesium sulfate. Purification was done by silica gel flash column chromatography (60:40, hexane-ethyl acetate) which afforded the pure yellow-colored phenol (0.179 g, 0.48 mmol) in 11% yield. The phenol had a melting point of 189-190° C.
後処理
- temperaturewas heated
- customAfter quenching with 1M HCl
- extractionthe product was extracted with CH2Cl2
- extractionThe combined extract
- washwas washed with water
- washrinsed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customPurification
出典と根拠
- ORDレコード
- ord-d5ce02cecbb44429899fff1cda686101
- 出典データセット
- uspto-grants-2008_11
- 特許番号
- US07456214B2
関連ノート
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