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

HRID 1448347Notes

Reaction equation

HRID 1448347 reaction equation
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]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 890951-Methyl-1H-pyrrole-2-acetic acidHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 194 parts of 1,1'-oxybisethane are added 9.1 parts of lithium aluminum 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.

Workup

  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

Sources & evidence

ORD record
ord-35c1b52930c147848aa22867e86ec7c6
Source dataset
uspto-grants-1979_12
Patent number
US04179569

Reaction notes

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