3,4,5-Trimethoxyphenol → 2'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalcone

HRID 1095273

反応式

HRID 1095273 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N+:14]([C:17]1[CH:27]=[CH:26][C:20]([CH:21]=[CH:22][C:23](Cl)=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[OH:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[C:4]=1[C:23](=[O:24])[CH:22]=[CH:21][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:27][CH:26]=1

参加物

3

反応物 2

HCID 695053,4,5-TrimethoxyphenolHCID 3194633-(4-nitrophenyl)prop-2-enoyl Chloride

生成物 1

HCID 727670692'-Hydroxy-4',5',6'-trimethoxy-4-nitrochalcone収率 22%

反応条件

温度
80 °C

実験手順

A mixture of 3,4,5-trimethoxyphenol (1.85 g, 10 mmol) and 4-nitrocinnamoyl chloride (2.11 g, 10 mmol) was dissolved in BF3-Et2O complex (10 ml) and heated to 80° C. for 10 min, and then quenched with excess of water. The aqueous layer was extracted with dichloromethane. The combined organic layer was concentrated and the residue was purified by column chromatography on silica gel (CH2Cl2:EtOAc:Hexane=1:1:3) gave 7a (0.79 g, 22%) and 7b (1.54 g, 43%). 1H NMR (400 MHz, CDCl3) μ 3.81 (s, 3H), 3.90 (s, 3H), 3.91 (s, 3H), 6.29 (s, 1H), 7.74 (d, J=8.8 Hz, 2H), 7.76 (d, J=16.0 Hz, 1H), 8.01 (d, J=16.0 Hz, 1H), 8.26 (d, J=8.8 Hz, 2H), 13.44 (s, 1H).

後処理

  1. dissolutionwas dissolved in BF3-Et2O complex (10 ml)
  2. customquenched with excess of water
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. concentrationThe combined organic layer was concentrated
  5. customthe residue was purified by column chromatography on silica gel (CH2Cl2:EtOAc:Hexane=1:1:3)

出典と根拠

ORDレコード
ord-4049c48a3e50449dade86f120b203cfc
出典データセット
uspto-grants-2012_03
特許番号
US08138165B2

関連ノート

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