Sodium Chloride → 1-Acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine

HRID 2165761노트

반응식

HRID 2165761 반응식
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:11](Cl)[CH:12]=[CH:13][CH3:14].[Mg].[Cl-].[Na+]>CCOCC.O1CCCC1>[C:1]([N:4]1[CH2:9][CH2:8][C:7]([OH:10])([CH:13]([CH3:14])[CH:12]=[CH2:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 11589Crotyl chlorideHCID 122563N-Acetyl-4-piperidoneHCID 5462224Magnesium

생성물 1

HCID 148520451-Acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1.94 g 1-acetyl-4-piperidone in a mixture of ether (80 ml) and tetrahydrofuran (40 ml), was added dropwise at 10° C. or lower 275 ml of a 0.5M Grignard reagent prepared by the usual way from crotyl chloride and magnesium, and the resulting mixture was stirred overnight at room temperature. To the ice-cooled reaction mixture, was slowly added 100 ml of saturated aqueous solution of sodium chloride, and the layers were separated. The aqueous layer was extracted with chloroform, the two organic solutions were each concentrated, and the combined concentrate was subjected to silica gel column chromatography using, as eluent, a mixed solvent of ethyl acetate/n-hexane (1:1 by volume) containing 3% methanol, giving 16.9 g of 1-acetyl-4-hydroxy-4-(1-methyl-2-propenyl)piperidine as oil.

후처리

  1. additionwas added dropwise at 10° C.
  2. customreaction mixture
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with chloroform
  5. concentrationthe combined concentrate
  6. additiona mixed solvent of ethyl acetate/n-hexane (1:1 by volume) containing 3% methanol

출처 및 근거

ORD 기록
ord-993f2c5111a94819ad11f54a9ab4885e
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04940795

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