Water → HCID 20394492, compound

HRID 261613Notes

Reaction equation

HRID 261613 reaction equation
C(O[C:4]([N:6]1[CH2:11][CH:10]=[C:9]([CH3:12])[CH2:8][CH:7]1[C:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([CH3:15])[CH3:14])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.CCOCC>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]([CH:7]2[CH2:8][C:9]([CH3:12])=[CH:10][CH2:11][N:6]2[CH3:4])([CH3:15])[CH3:14])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 20394497HCID 20394497, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20394492HCID 20394492, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-Ethoxycarbonyl-1,2,3,6-tetrahydro-2-[1-(4-methoxyphenyl)-1-methylethyl]-4-methylpyridine (3.17 g) dissolved in 10 ml of dried tetrahydrofuran was added dropwise to a suspension of 0.9 g of lithium aluminium hydride in 5 ml of dried tetrahydrofuran while stirring under cooling with ice and then the mixture was refluxed for 30 minutes. After cooling, water-containing ether (150 ml) and then 10 ml of a 30% sodium hydroxide aqueous solution was added dropwise to the mixture while stirring under cooling with ice. An diethyl ether-tetrahydrofuran layer was decanted and combined with the diethyl ether portions with which the remaining matter had been washed. The combined liquid was dried over potassium carbonate, stripped of the solvent and distilled under reduced pressure to obtain 2.1 g of 1,2,3,6-tetrahydro-2-[1-(4-methoxyphenyl)-1-methylethyl]-1,4-dimethylpyridine as a colorless viscous mass.

Workup

  1. temperatureunder cooling with ice
  2. temperaturethe mixture was refluxed for 30 minutes
  3. temperatureAfter cooling
  4. stirringwhile stirring
  5. temperatureunder cooling with ice
  6. customAn diethyl ether-tetrahydrofuran layer was decanted
  7. washhad been washed
  8. dry with materialThe combined liquid was dried over potassium carbonate
  9. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-9eac33f0646449f0b7f85d1d99b48ad5
Source dataset
uspto-grants-1979_08
Patent number
US04166174

Reaction notes

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