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

HRID 1658908Notes

Reaction equation

HRID 1658908 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 8028TetrahydrofuranSolvent2×

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 tetrahydrofurane 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. m.p. = 15°C

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-8e20aceb43534614b8512a7978074988
Source dataset
uspto-grants-1976_06
Patent number
US03966766

Reaction notes

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