p-Pentyloxyphenol → 4-pentoxyphenyl (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylate

HRID 2246015ノート

反応式

HRID 2246015 の反応式
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10](O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:14]([O:16][C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[CH:22][CH:21]=1)=[O:18])[CH3:15].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[CH2:14]([O:16][C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:8][CH:9]=2)=[O:29])=[CH:22][CH:21]=1)=[O:18])[CH3:15]

参加物

6

反応物 3

HCID 29353p-PentyloxyphenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12876666(2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoic acid

生成物 1

HCID 592174614-pentoxyphenyl (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylate収率 94.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

23.00 g (97 mmol) 4-pentoxyphenol, 17.6 g (97 mmol) (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylic acid and 1.18 g (9.7 mmol) 4-dimethylaminopyridine were dissolved in 300 ml of dichloromethane. A suspension of 18.6 g (97 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbo-diimide hydrochloride and 200 ml dichloromethane were added dropwise in the course of 40 minutes. After 22 h at room temperature, the reaction mixture was partitioned between dichloromethane and water; the organic phase was washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation. Chromatography of the residue on 200 g silica gel using cyclohexane:ethyl acetate (7:3) then (1:1) as eluent yielded 36.4 g (94%) 4-pentoxyphenyl (2E)-3-{4-[(ethoxycarbonyl)oxy]phenyl}acrylate as colourless crystals.

後処理

  1. additionwere added dropwise in the course of 40 minutes
  2. customthe reaction mixture was partitioned between dichloromethane and water
  3. washthe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-4fc89421594c44ed9221b757aa10c03b
出典データセット
uspto-grants-2010_03
特許番号
US07687118B2

反応ノート

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