Hydrochloric Acid → (-)-2-Cyano-2-methylpentyl p-toluenesulfonate

HRID 1461201Notes

Reaction equation

HRID 1461201 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.Cl.[C:13]([C:15]([CH3:21])([CH2:18][CH2:19][CH3:20])[CH2:16][OH:17])#[N:14]>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:17][CH2:16][C:15]([C:13]#[N:14])([CH3:21])[CH2:18][CH2:19][CH3:20])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 14793480HCID 14793480, compound

Product 1

HCID 14793472(-)-2-Cyano-2-methylpentyl p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a round-bottomed flask, 1.35 mg (10.6 mM) of (-)-2-cyano-2-methylpentanol was dissolved in 2.52 g of dry pyridine. The mixture was placed on an ice bath, and 2.22 g (11.7 mM) of p-toluenesulfonyl chloride was added, followed by 6 hours of stirring at room temperature. After the reaction, 10 ml of 6N-hydrochloric acid was added, followed by 3 times of extraction with 15 ml of diethyl ether. The extract was dried overnight on anhydrous sodium sulfate, followed by distilling-off of the solvent and purification by column chromatography by using 80 g of silica gel and a dichloromethane/benzene (2/1) solvent to obtain (-)-2-cyano-2-methylpentyl p-toluenesulfonate. Yield: 2.57 g (9.1 mM), 86%

Workup

  1. customThe mixture was placed on an ice bath
  2. additionwas added
  3. extractionfollowed by 3 times of extraction with 15 ml of diethyl ether
  4. dry with materialThe extract was dried overnight on anhydrous sodium sulfate
  5. distillationfollowed by distilling-off of the solvent and purification by column chromatography

Sources & evidence

ORD record
ord-aa6bc227928f47d2b2016e30c3ffd9a7
Source dataset
uspto-grants-1991_12
Patent number
US05075031

Reaction notes

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