Ethylene Oxide → 1-Diethylamino-3-(4-nitro-phenoxy)-propan-2-ol

HRID 640939

反応式

HRID 640939 の反応式
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH:10]2[CH2:12][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:15]([NH:17][CH2:18][CH3:19])[CH3:16].O1CC1>CCO>[CH2:15]([N:17]([CH2:18][CH3:19])[CH2:12][CH:10]([OH:11])[CH2:9][O:8][C:7]1[CH:13]=[CH:14][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[CH3:16]

参加物

5

反応物 3

HCID 6354Ethylene OxideHCID 8021DiethylamineHCID 213272-((4-Nitrophenoxy)methyl)oxirane2 回

生成物 1

HCID 150724871-Diethylamino-3-(4-nitro-phenoxy)-propan-2-ol収率 89%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-(4-nitro-phenoxymethyl)-oxirane (9.75 g, 50 mmol) in absolute EtOH (100 mL) was heated at 70° C. until 2-(4-nitro-phenoxymethyl)-oxirane is dissolved then the solution was allowed to cool to room temperature. Subsequently the room temperature solution was treated with diethylamine (5.2 mL, 1.0 equiv.) in one portion. The reaction mixture is stirred at room temperature for 15 min during which time starting material (oxirane) began to precipitate out of solution. The reaction mixture was heated to 50° C. and an additional amount of diethylamine (2.6 mL) was added to achieve complete dissolution of starting oxirane. The reaction mixture was heated for an additional 5 h at 55° C. at which point thin layer chromatography (9:1, chloroform: methanol) indicated complete consumption of the starting oxirane. The reaction mixture was cooled to room temperature and concentrated in vacuo. The oily light brown residue obtained after evaporation, was purified by flash silica gel chromatography, (CHCl3 to 1:9, MeOH:CHCl3 gradient eluant) to give the 1-diethylamino-3-(4-nitro-phenoxy)-propan-2-ol as a yellow oil (11.9 g, 89%).

後処理

  1. dissolutionis dissolved
  2. customto precipitate out of solution
  3. temperatureThe reaction mixture was heated to 50° C.
  4. additionan additional amount of diethylamine (2.6 mL) was added
  5. dissolutiondissolution of starting oxirane
  6. temperatureThe reaction mixture was heated for an additional 5 h at 55° C. at which point thin layer chromatography (9:1, chloroform: methanol)
  7. customconsumption of the starting oxirane
  8. temperatureThe reaction mixture was cooled to room temperature
  9. concentrationconcentrated in vacuo
  10. customThe oily light brown residue obtained
  11. customafter evaporation
  12. customwas purified by flash silica gel chromatography, (CHCl3 to 1:9, MeOH:CHCl3 gradient eluant)

出典と根拠

ORDレコード
ord-985ad3c7462549748d6aac79e615bd54
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

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