Ethylene Glycol → 3-Quinuclidinone ethyleneketal

HRID 1602192Notes

Reaction equation

HRID 1602192 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C:4](=[O:10])[CH2:3]2.[OH-].[Na+].[CH2:13](O)[CH2:14][OH:15]>>[CH2:14]1[O:15][C:4]2([CH:5]3[CH2:8][CH2:9][N:2]([CH2:7][CH2:6]3)[CH2:3]2)[O:10][CH2:13]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 1020191-Azabicyclo(2.2.2)octan-3-one, hydrochloride (1:1)

Product 1

HCID 64217473-Quinuclidinone ethyleneketalYield 100%

Conditions

Temperature
200 °C

Procedure

A mixture of 3-quinuclidinone hydrochloride (5 g, 31 mmol) and ethylene glycol (20 ml) was heated under nitrogen at 200° C. (bath temperature) for 2 h. After cooling, the reaction mixture was poured in an excess of 1 M aqueous sodium hydroxide. Extraction with three portions of ethyl acetate was followed by drying over magnesium sulfate, and evaporation of the solvent to yield the product (5.2 g, 31 mmol, 100%) as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. extractionExtraction with three portions of ethyl acetate
  3. dry with materialby drying over magnesium sulfate, and evaporation of the solvent

Sources & evidence

ORD record
ord-47086514b4194553ad538c2734b2524f
Source dataset
uspto-grants-1999_11
Patent number
US05981539

Reaction notes

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