Lithium → HCID 23044990, compound
Reaction equation
[Li].[N:2]([N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][O:7][CH2:6][C:5]1([CH3:13])[CH3:12])=O>O1CCCC1.C(OCCCC)CCC>[NH2:2][N:4]1[C:5]([CH3:13])([CH3:12])[CH2:6][O:7][CH2:8][C:9]1([CH3:11])[CH3:10]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 99 °C
Procedure
About 20% of a solution of 5 g of lithium alanate in 50 ml of tetrahydrofuran is added dropwise to a heated solution of 17.2 g of 4-nitroso-3,3,5,5-tetramethylmorpholine in 50 ml of tetrahydrofuran and 100 ml of dibutyl ether. The tetrahydrofuran is distilled off and the internal temperature is increased to 99° C. The remainder of the lithium alanate solution is then added dropwise and the mixture is kept at 70° C. for a further hour. After the mixture has been cooled in an ice-bath, 10 ml of water and 10 ml of 15% strength sodium hydroxide solution are carefully added. After filtration with suction, the filtrate is extracted by shaking first with water and then with 100 ml of 1N hydrochloric acid. The aqueous HCl phase is then extracted by shaking once more with diethyl ether and used in the next stage.
Workup
- distillationThe tetrahydrofuran is distilled off
- additionThe remainder of the lithium alanate solution is then added dropwise
- waitthe mixture is kept at 70° C. for a further hour
- temperatureAfter the mixture has been cooled in an ice-bath
- addition10 ml of water and 10 ml of 15% strength sodium hydroxide solution are carefully added
- filtrationAfter filtration with suction
- extractionthe filtrate is extracted
- extractionThe aqueous HCl phase is then extracted
- stirringby shaking once more with diethyl ether
Sources & evidence
- ORD record
- ord-1008bfcf2e4343009632d27e32ecc48b
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04937244
Reaction notes
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