Diethyl Ether → 2-(1-methyl-1H-pyrrol-2-yl)ethan-1-ol

HRID 1973849노트

반응식

HRID 1973849 반응식
O(CC)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][C:19](O)=[O:20].[OH-].[Na+]>O>[CH3:12][N:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][CH2:19][OH:20]

참가 물질

6

반응물 4

HCID 3283Diethyl Ether2회HCID 14798Sodium HydroxideHCID 890951-Methyl-1H-pyrrole-2-acetic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 117685722-(1-methyl-1H-pyrrol-2-yl)ethan-1-ol수율 69%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To 194 parts of 1,1'-oxybisethane are added 9.1 parts of lithium aluminium hydride while nitrogen gas is introduced. Then there is added dropwise, during a 2 hours-period, a solution of 14.9 parts of 1-methyl-1H-pyrrole-2-acetic acid in 105 parts of 1,1'-oxybisethane (exothermic reaction). Upon completion, stirring is continued for 8 hours at reflux temperature and for 8 hours at room temperature. The reaction mixture is cooled in an ice-salt bath and decomposed by successive dropwise additions of 9.5 parts of water, 8.5 parts of a sodium hydroxide solution 20% and again 33.3 parts of water. The precipitated product is filtered off and suspended in 1,1'-oxybisethane. The combined 1,1'-oxybisethane phases are dried, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (93:7) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 9.5 parts (69%) of 1-methyl-1H-pyrrole- 2-ethanol as a residue.

후처리

  1. additionis introduced
  2. additionThen there is added dropwise, during a 2 hours-period
  3. temperatureat reflux temperature
  4. waitfor 8 hours at room temperature
  5. temperatureThe reaction mixture is cooled in an ice-salt bath
  6. filtrationThe precipitated product is filtered off
  7. dry with materialThe combined 1,1'-oxybisethane phases are dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (93:7) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated

출처 및 근거

ORD 기록
ord-67726c8e1a264f29a01dd861d0b007c9
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03998834

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