Aluminium lithium hydride → 1,4,7,13,16,19-Hexaoxa-10,22-diazacyclotetracosane

HRID 263270Notes

Reaction equation

HRID 263270 reaction equation
O=[C:2]1[CH2:25][O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][C:16](=O)[NH:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[O:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:2][NH:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21316285HCID 21316285, compound

Product 1

HCID 43782741,4,7,13,16,19-Hexaoxa-10,22-diazacyclotetracosaneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 30 g. of the diamide obtained in Example 15 in 200 ml. anhydrous tetrahydrofurane is slowly added to a mixture of 50 ml. anhydrous tetrahyfrofurane and 18 g. LiAlH4 while stirring and heating at the reflux temperature. After the addition is completed, the mixture is stirred under reflux and under a nitrogen atmosphere for 24 hours. After cooling to room temperature the reducing agent is destroyed by adding a mixture of water and THF (1:2). The mixture is filtered and the filtrate is evaporated to dryness. The residue is dissolved in benzene and the solution is passed through a column of Al2O3 with benzene as eluant. The solution is evaporated to dryness and the desired product is obtained as a colourless oil which crystallizes at low temperatures.

Workup

  1. temperatureheating at the reflux temperature
  2. additionAfter the addition
  3. temperatureunder reflux and under a nitrogen atmosphere for 24 hours
  4. customis destroyed
  5. additionby adding
  6. additiona mixture of water and THF (1:2)
  7. filtrationThe mixture is filtered
  8. customthe filtrate is evaporated to dryness
  9. dissolutionThe residue is dissolved in benzene
  10. customThe solution is evaporated to dryness

Sources & evidence

ORD record
ord-4fecb69516c7454ebbee45e559541ea7
Source dataset
uspto-grants-1979_05
Patent number
US04156683

Reaction notes

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