2-Isopropylphenol → JW 480

HRID 1771943ノート

反応式

HRID 1771943 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([CH3:3])[CH3:2].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.CCN(CC)CC.[C:31]([O-:34])(O)=O.[Na+].C(=O)([O-])[O-].[CH:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][C:41]=1[CH2:50][CH2:51][NH2:52]>ClCCl.C(OCC)(=O)C>[CH:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:43]=[CH:42][C:41]=1[CH2:50][CH2:51][NH:52][C:31](=[O:34])[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2]

参加物

9

反応物 6

HCID 69432-IsopropylphenolHCID 8471Triethylamine2 回HCID 19660Carbonate IonHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium Bicarbonate2 回HCID 37843782-(2-Naphthyl)ethyl-amine

生成物 1

HCID 57330099JW 480収率 94%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-isopropylphenol (5.0 g, 36.713 mmol) in dichloromethane (183.0 mL) was added 4-nitrophenyl chloroformate (8.1 g, 40.385 mmol) and Et3N (10.3 mL, 73.426 mmol) at 0° C. After stirring at 0° C. 2 hours, the reaction mixture was treated with 30.0 mL of saturated aqueous NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was used without further purification. To a solution of crude carbonate intermediate in dichloromethane (150 mL) was added 2-(naphthalen-2-yl)ethanamine (6.9 g, 40.385 mmol) and Et3N (10.3 mL, 73.426 mmol) at 0° C. After stirring at 0° C. 2 hours, the reaction mixture was treated with 30.0 mL of saturated aqueous NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 9:1 v/v hexane:ethyl acetate as solvent to afford title compound (11.5 g, 94% yield) as a white solid.

後処理

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was used without further purification
  8. stirringAfter stirring at 0° C
  9. customThe organic layer was separated
  10. extractionthe aqueous layer was extracted with dichloromethane
  11. washThe combined organic extracts were washed with brine
  12. dry with materialdried over MgSO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe crude product was purified by flash column chromatography

出典と根拠

ORDレコード
ord-b798813aa4ef42dc961fc9c264b57371
出典データセット
uspto-grants-2016_02
特許番号
US09249128B2

反応ノート

読み込み中…