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

HRID 1095273

반응식

HRID 1095273 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4049c48a3e50449dade86f120b203cfc
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138165B2

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