Aluminium lithium hydride → Diaza-18-crown-6

HRID 1658906Notes

Reaction equation

HRID 1658906 reaction equation
O=[C:2]1[CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][C:13](=O)[NH: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][NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:2][NH:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 213163171,4,10,13-Tetraoxa-7,16-diazacyclooctadecane-6,17-dione

Product 1

HCID 72805Diaza-18-crown-6Yield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 18.5 g. of the diamide obtained in Example 3 in 450 ml. anhydrous tetrahydrofurane is slowly added to a mixture of 150 ml. anhydrous tetrahydrofurane and 12 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 excess reagent 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 after recrystallization from benzene/petrol ether 13.5 g. of the desired product is obtained. m.p. = 115°C-116°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
  11. customafter recrystallization from benzene/petrol ether 13.5 g

Sources & evidence

ORD record
ord-e6bcab5e5a57446aadbe5b840c6951c1
Source dataset
uspto-grants-1976_06
Patent number
US03966766

Reaction notes

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