Water → HCID 13326774, compound

HRID 2291139Notes

Reaction equation

HRID 2291139 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1([CH2:17][CH:18]2[O:22][CH2:21][CH2:20][O:19]2)[CH2:14][CH:13]2[CH2:15][CH2:16][CH:10]1[CH2:11][CH2:12]2)#[N:8].O.[OH-].[Na+]>CCOCC>[NH2:8][CH2:7][C:9]1([CH2:17][CH:18]2[O:19][CH2:20][CH2:21][O:22]2)[CH2:14][CH:13]2[CH2:12][CH2:11][CH:10]1[CH2:16][CH2:15]2

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13326773HCID 13326773, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13326774HCID 13326774, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3.7 g of lithium aluminum hydride are suspended in 60 ml of dry ether; 7.4 g of 2-cyano-2-(1,3-dioxolan-2-yl)methylbicyclo[2.2.2]octane, dissolved in 80 ml of dry ether, are added dropwise so that gentle boiling is maintained. The mixture is then boiled under reflux for 2 hours, then cooled in ice and, in sequence, 2.1 ml of water, 2.1 ml of 1N sodium hydroxide solution and 15 ml of water are added dropwise. The aluminum hydroxide is filtered off with suction and thoroughly washed with ether. 5.5 g of the title compound are obtained as a colorless oil.

Workup

  1. additionare added dropwise so that gentle boiling
  2. temperatureis maintained
  3. temperatureunder reflux for 2 hours
  4. additionare added dropwise
  5. filtrationThe aluminum hydroxide is filtered off with suction
  6. washthoroughly washed with ether

Sources & evidence

ORD record
ord-57b512243c124d82abed41b3e4e35094
Source dataset
uspto-grants-1986_10
Patent number
US04620012

Reaction notes

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