Sodium hydride → methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate

HRID 382807노트

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HRID 382807 반응식
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[CH2:14]([C:16]1[C:21]([O:22][CH3:23])=[CH:20][C:19]([CH:24]2[C:29](=O)[CH2:28][CH2:27][N:26]([CH3:31])[CH2:25]2)=[CH:18][C:17]=1[O:32][CH3:33])[CH3:15]>O1CCCC1>[CH2:14]([C:16]1[C:17]([O:32][CH3:33])=[CH:18][C:19]([CH:24]2[CH2:25][N:26]([CH3:31])[CH2:27][CH2:28]/[C:29]/2=[CH:5]\[C:3]([O:2][CH3:1])=[O:4])=[CH:20][C:21]=1[O:22][CH3:23])[CH3:15]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 183619573-(4-Ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-one

생성물 1

HCID 86757543methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate수율 91.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 39 ml (262.4 mmol) of trimethyl phosphonoacetate in 450 ml of tetrahydrofuran was added dropwise at 0° to a suspension of 9.54 g (238.5 mmol) of sodium hydride (55% in mineral oil) in 450 ml of tetrahydrofuran and the mixture was stirred for 30 minutes. Subsequently, the white suspension was treated with a solution of 33.15 g (119.5 mmol) of 3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-one in 450 ml of tetrahydrofuran and the mixture was stirred at 50° for 2 hours. After cooling to room temperature the mixture was poured on to 500 ml of ice-water and extracted three times with 400 ml of diethyl ether. The organic phases were washed with 400 ml of water and 400 ml of saturated sodium chloride solution, dried (Na2SO4), filtered and evaporated. Chromatography (silica gel, methylene chloride/methanol 19:1) and recrystalization from hexane yielded 36.33 g (91%) of methyl (E)-[3-(4-ethyl-3,5-dimethoxy-phenyl)-1-methyl-piperidin-4-ylidene]acetate as pale yellow crystals of m.p. 110-112°.

후처리

  1. stirringthe mixture was stirred at 50° for 2 hours
  2. extractionextracted three times with 400 ml of diethyl ether
  3. washThe organic phases were washed with 400 ml of water and 400 ml of saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customChromatography (silica gel, methylene chloride/methanol 19:1) and recrystalization from hexane

출처 및 근거

ORD 기록
ord-87c16e7dc7ff4b7b86bfcc7e258a59bf
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310208B1

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