Hexane → 2-(2,4-Dinitrophenyl)ethyl (2E)3-{4-[(4-(4,4,5,5,5-pentafluoropentoxy)benzoyl)oxy]phenyl}acrylate

HRID 2193510ノート

反応式

HRID 2193510 の反応式
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][CH2:14][OH:15])([O-:3])=[O:2].[F:16][C:17]([F:46])([C:42]([F:45])([F:44])[F:43])[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:41]=[CH:40][C:25]([C:26]([O:28][C:29]2[CH:34]=[CH:33][C:32](/[CH:35]=[CH:36]/[C:37](O)=[O:38])=[CH:31][CH:30]=2)=[O:27])=[CH:24][CH:23]=1.Cl.CN(C)CCCN=C=NCC.CCCCCC>CN(C)C1C=CN=CC=1.ClCCl>[F:16][C:17]([F:46])([C:42]([F:43])([F:44])[F:45])[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:41]=[CH:40][C:25]([C:26]([O:28][C:29]2[CH:34]=[CH:33][C:32](/[CH:35]=[CH:36]/[C:37]([O:15][CH2:14][CH2:13][C:5]3[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])=[O:38])=[CH:31][CH:30]=2)=[O:27])=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 118307342-(2,4-Dinitrophenyl)ethanolHCID 86625095(2E)-3-(4-{[4-(4,4,5,5,5-pentafluoropentoxy)benzoyl]oxy}phenyl)acrylic acid

生成物 1

HCID 581935662-(2,4-Dinitrophenyl)ethyl (2E)3-{4-[(4-(4,4,5,5,5-pentafluoropentoxy)benzoyl)oxy]phenyl}acrylate収率 71%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2.50 g (11.8 mmol) of 2-(2,4-dinitrophenyl)ethanol, 5.24 g (11.8 mmol) of (2E)-3-(4-{[4-(4,4,5,5,5-pentafluoropentoxy)benzoyl]oxy}phenyl)acrylic acid, 144 mg (1.2 mmol) of 4-Dimethylaminopyridine are dissolved in 30 ml of dichloromethane. 2.48 g (13.0 mmol) of N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC hydrochloride) are added at 0° C. The solution is stirred for 1 h at 0° C. and allowed to stir at room temperature overnight. After 22 hours at room temperature the reaction mixture is partitioned between dichloromethane and water. The organic phase is washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using toluene:ethyl acetate 95:5 as eluant and crystallization form ethylacetate:hexane mixture to yield 5.35 g (71%) 2-(2,4-Dinitrophenyl)ethyl (2E)3-{4-[(4-(4,4,5,5,5-pentafluoropentoxy)benzoyl)oxy]phenyl}acrylate as colorless crystals.

後処理

  1. stirringto stir at room temperature overnight
  2. customAfter 22 hours at room temperature the reaction mixture is partitioned between dichloromethane and water
  3. washThe organic phase is washed repeatedly with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customcrystallization
  8. customform ethylacetate

出典と根拠

ORDレコード
ord-008f0ca443d1402dabe5f0a25acd23c1
出典データセット
uspto-grants-2012_12
特許番号
US08329823B2

反応ノート

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