Sodium Chloride → 3-[p-[3-(2-Hydroxyethyl)oxy-2-methyl-1-propenyl]benzyl]pyridine

HRID 569173노트

반응식

HRID 569173 반응식
C([O:4][CH2:5][CH2:6][O:7][CH2:8][CH:9]([CH3:25])[CH:10]([C:12]1[CH:24]=[CH:23][C:15]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1)O)(=O)C.S(Cl)(Cl)=O.C1CCN2C(=NCCC2)CC1.[Cl-].[Na+]>C(Cl)Cl.CN(C)C=O.O>[OH:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([CH3:25])=[CH:10][C:12]1[CH:24]=[CH:23][C:15]([CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 24386Thionyl ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 137455233-[p-[3-(2-Acetoxyethyl)oxy-1-hydroxy-2-methylpropyl]benzyl]pyridine

생성물 1

HCID 536849613-[p-[3-(2-Hydroxyethyl)oxy-2-methyl-1-propenyl]benzyl]pyridine수율 50%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

In 10 ml of methylene chloride was dissolved 2.07 g of 3-[p-[3-(2-acetoxyethyl)oxy-1-hydroxy-2-methylpropyl]benzyl]pyridine, and to the resulting solution was added 0.88 ml of thionyl chloride with ice-cooling, after which the resulting mixture was subjected to reaction at the same temperature for one hour. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure. The residue thus obtained was dissolved in 10 ml of N,N-dimethylformamide, and to the resulting solution was dropwise added 4.5 ml of DBU, after which the resulting mixture was subjected to stirring at 100° to 110° C. for 2 hours. Subsequently, 5 ml of water was dropped into the mixture, and the mixture was subjected to reaction at 100° C. for 2 hours. The reaction mixture was poured into 80 ml of a saturated aqueous sodium chloride solution, and the resulting mixture was subjected to extraction with two 40-ml portions of ethyl acetate. The extracts were combined, washed with 20 ml of water and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform] to obtain 850 mg (yield 50.0%) of colorless, oily 3-[p-[3-(2-hydroxyethyl)oxy-2 -methyl-1-propenyl]benzyl]pyridine.

후처리

  1. temperaturecooling
  2. customafter which the resulting mixture was subjected to reaction at the same temperature for one hour
  3. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure
  4. customThe residue thus obtained
  5. customthe mixture was subjected to reaction at 100° C. for 2 hours
  6. extractionthe resulting mixture was subjected to extraction with two 40-ml portions of ethyl acetate
  7. washwashed with 20 ml of water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customthe residue thus obtained
  11. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: chloroform]

출처 및 근거

ORD 기록
ord-4941c5752b9c4a13857b4933f9ba342c
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731370

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