Aluminium lithium hydride → 1,4,7,13,16-Pentaoxa-10,19-diazacyclohenicosane
Reaction equation
O=[C:2]1[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][CH2:2][NH:3][CH2:4][CH2:5]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 6.7 g. of the diamide obtained in Example 19 in 100 ml. anhydrous tetrahydrofurane is slowly added to a mixture of 50 ml. anhydrous tetrahydrofurane and 3.8 g. LiAlH4 while stirring. After the addition is complete, the mixture is stirred under reflux and under a nitrogen atmosphere for 11 hours. After cooling to room temperature, the reagent is destroyed by adding 10 ml. water in 25 ml. THF, followed by 10 ml. NaOH (15% in water) and then 30 ml. water. 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 temperature.
Workup
- additionAfter the addition
- temperatureunder reflux and under a nitrogen atmosphere for 11 hours
- customthe reagent is destroyed
- additionby adding 10 ml
- filtrationThe mixture is filtered
- customthe filtrate is evaporated to dryness
- dissolutionThe residue is dissolved in benzene
- customThe solution is evaporated to dryness
Sources & evidence
- ORD record
- ord-c9b5a300ba9f47f7b2c63054bdc4429c
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04156683
Reaction notes
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