Hydrochloric Acid → HCID 20137673, compound
Reaction equation
[CH2:1]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].C([Li])CCC.[C:22](OCC)(=[O:24])[CH3:23].Cl>O1CCCC1.CCCCCC.O>[C:22]([CH:14]([CH2:13][CH2:12][CH2:11][O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[C:15]#[N:16])(=[O:24])[CH3:23]Participants
Conditions
- Temperature
- -60 °C
Procedure
35.0 g (156 millimoles) of 5-(n-nonyloxy)-valeronitrile in 500 ml of absolute tetrahydrofuran are initially taken, in the absence of water and under an inert gas atmosphere, and the mixture is cooled to -60° C. 162 millimoles of n-butyl-lithium in n-hexane are slowly added to the stirred mixture, which is then left for 4 hours at -60° C. A solution of 13.1 g (155 millimoles) of dry ethyl acetate in tetrahydrofuran is then added dropwise, stirring is continued for 3 hours at -60° C., and the mixture is allowed to warm up slowly to room temperature. First water and then 2N hydrochloric acid are added while cooling with ice, until the pH of the solution reaches 4. The organic phase which separates out is isolated, washed with water, dried and evaporated down. The oil which remains (41 g; 99%) is more than 90% pure according to gas chromatography, and can be reacted without further purification.
Workup
- waitis continued for 3 hours at -60° C.
- temperatureto warm up slowly to room temperature
- temperaturewhile cooling with ice, until the pH of the solution
- customThe organic phase which separates out is isolated
- washwashed with water
- customdried
- customevaporated down
- customcan be reacted without further purification
Sources & evidence
- ORD record
- ord-25f57552c1bb430eb838e9416117862d
- Source dataset
- uspto-grants-1988_05
- Patent number
- USRE032676
Reaction notes
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