Water → N-[4-[[(E)-3-(4-Isopropylphenyl)-2-propenyl]oxy]-2,3,6-trimethylphenyl]formamide

HRID 272351노트

반응식

HRID 272351 반응식
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4]([CH3:12])[C:3]=1[CH3:13].[H-].[Na+].Br[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=1.O>CN(C)C=O>[CH:26]([C:23]1[CH:22]=[CH:21][C:20](/[CH:19]=[CH:18]/[CH2:17][O:1][C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][CH:10]=[O:11])=[C:4]([CH3:12])[C:3]=2[CH3:13])=[CH:25][CH:24]=1)([CH3:28])[CH3:27]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21961295N-(4-hydroxy-2,3,6-trimethylphenyl)formamideHCID 219613131-[(E)-3-bromo-1-propenyl]-4-isopropylbenzene

생성물 1

HCID 21961342N-[4-[[(E)-3-(4-Isopropylphenyl)-2-propenyl]oxy]-2,3,6-trimethylphenyl]formamide수율 59.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-(4-hydroxy-2,3,6-trimethylphenyl)formamide (5.20 g, 29.0 mmol) in N,N-dimethylformamide (30 ml) was added at 0° C. under a nitrogen atmosphere sodium hydride (a 60% dispersion in liquid paraffin, 1.39 g, 34.8 mmol) and the resulting mixture was stirred at the same temperature for 10 minutes. To the reaction solution was added 1-[(E)-3-bromo-1-propenyl]-4-isopropylbenzene (9.00 g, 37.7 mmol) and the resulting mixture was stirred at room temperature for 30 minutes. Water was added into the reaction solution and the product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was crystallized from ethyl acetate-hexane to obtain 5.80 g (59% yield) of the title compound. Melting point: 165-167° C.

후처리

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. extractionthe product was extracted twice with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried on magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was crystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-dfd0ca46395e4a76a44a12a4b2353bcf
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456162B2

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