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

HRID 2246015노트

반응식

HRID 2246015 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4fc89421594c44ed9221b757aa10c03b
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687118B2

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