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Water → 1-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-1-(3-pyridyl)heptanol

HRID 1030600
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인쇄 미리보기

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HRID 1030600 반응식
[Mg].Br[C:3]1[C:8]([CH3:9])=[C:7]([O:10][CH3:11])[C:6]([CH3:12])=[C:5]([CH3:13])[C:4]=1[O:14][CH3:15].[C:16]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)(=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O>O1CCCC1>[CH3:15][O:14][C:4]1[C:5]([CH3:13])=[C:6]([CH3:12])[C:7]([O:10][CH3:11])=[C:8]([CH3:9])[C:3]=1[C:16]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)([OH:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 2227091-(Pyridin-3-yl)heptan-1-oneHCID 2973651-Bromo-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 5462224Magnesium

생성물 1

HCID 145762641-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-1-(3-pyridyl)heptanol수율 39.3%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A Grignard reagent was prepared from 693 mg (28.3 g atom) of magnesium, 7.6 g (29.3 mmol) of 1-bromo-2,5-dimethoxy-3,4,6-trimethylbenzene and tetrahydrofuran at 65° C. and cooled to 0° C., to which a solution of 3.75 g (21.9 mmol) of 3-heptanoylpyridine in 10 ml of tetrahydrofuran was added dropwise. After completion of the addition, the reaction mixture was stirred at room temperature for 1 hour, to which water was added and extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified with silica gel column chromatography (isopropyl ether) and recrystallized from hexane, to give 3.2 g (39%) of 1-(2,5-dimethoxy-3,4,6-trimethylphenyl)-1-(3-pyridyl)heptanol. m.p. 109°-110° C.

후처리

  1. additionwas added dropwise
  2. additionAfter completion of the addition
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatography (isopropyl ether)
  9. customrecrystallized from hexane

출처 및 근거

ORD 기록
ord-c3aa564882f84447b622611e2a58e347
출처 데이터셋
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05106858

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