Hydrochloric Acid → 2-Cyano-2-methylhexyl p-toluenesulfonate
Reaction equation
[C:1]([C:3]([CH3:10])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])#[N:2].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1>[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17]([O:5][CH2:4][C:3]([C:1]#[N:2])([CH3:10])[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:19])=[O:18])=[CH:13][CH:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
535 mg (3.8 mM) of (-)-2-cyano-2-methylhexanol ([α]435 -1.9 degree (c=2.393, methylene chloride)) and 911 mg (11.4 mM) of dry pyridine were stirred at room temperature, followed by addition of 724 mg (3.8 mM) of p-toluenesulfonyl chloride and 7 hours of reaction. After the reaction, 6 ml of 2M-hydrochloric acid was added and extraction with ether was effected. The organic layer was washed with a small amount of 2M-hydrochloric acid and distilled water, followed by drying on sodium sulfate and distilling-off of the solvent under reduced pressure The product was then purified by thin layer chromatography (developer solvent: hexane/methylene chloride=1/5) to obtain 748 mg of (+) 2-cyano-2-methylhexyl p-toluenesulfonate. Yield: 63.3%, [α]D +10.7 degrees (c 2.182, benzene).
Workup
- additionwas added
- extractionextraction with ether
- washThe organic layer was washed with a small amount of 2M-hydrochloric acid
- distillationdistilled water
- customby drying on sodium sulfate and distilling-off of the solvent under reduced pressure The product
- customwas then purified by thin layer chromatography (developer solvent: hexane/methylene chloride=1/5)
Sources & evidence
- ORD record
- ord-4190fa31cc9c4347afe27000cef9bdfa
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05075031
Reaction notes
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