Hydroquinone → 4,4'-((((4-Methoxyphenyl)azanediyl)bis(ethane-2,1-diyl))bis(oxy))diphenol

HRID 1053595ノート

反応式

HRID 1053595 の反応式
Cl[CH2:2][CH2:3][N:4]([CH2:13][CH2:14]Cl)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[C:16]([O-:19])([O-])=O.[K+].[K+].[C:22]1([CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=1)[OH:23]>CN(C=O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([N:4]([CH2:13][CH2:14][O:11][C:8]2[CH:9]=[CH:10][C:16]([OH:19])=[CH:6][CH:7]=2)[CH2:3][CH2:2][O:23][C:22]2[CH:29]=[CH:28][C:26]([OH:27])=[CH:25][CH:24]=2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 15064N,N-Bis(2-chloroethyl)-4-methoxybenzenamine

生成物 1

HCID 717360914,4'-((((4-Methoxyphenyl)azanediyl)bis(ethane-2,1-diyl))bis(oxy))diphenol収率 16.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of compound 26a (100 mg, 0.6 mmol), K2CO3 (110 mg, 0.8 mmol), and KI (15 mg, 0.02 mmol) in DMF (50 mL) was bubbled with argon for 10 min. Hydroquinone (220 mg, 2 mmol) was added to the mixture under argon. The reaction mixture was heated and stirred at 80° C. for 6 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/EtOAc (3:1) to provide the compound 26 (20 mg, 0.05 mmol, 13% yield). 1H NMR (CDCl3, 400 MHz) δ 6.82-6.87 (m, 2H), 6.72-6.78 (m, 10H), 4.90 (bs, 2H), 4.07 (t, J=6.0 Hz, 4H), 3.76 (t, J=8.0 Hz, 7H).

後処理

  1. customwas bubbled with argon for 10 min
  2. temperatureThe reaction mixture was heated
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was evaporated
  5. customthe residue was quenched with 100 mL water
  6. extractionThe mixture was then extracted with EtOAc
  7. washthe combined organic layer was washed with water
  8. dry with materialbrine, and dried over Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue was purified by silica gel column chromatography with hexane/EtOAc (3:1)

出典と根拠

ORDレコード
ord-c06cf6c17c0749cf9e5a2d46983850f5
出典データセット
uspto-grants-2016_07
特許番号
US09394233B2

反応ノート

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