Pyridine → HCID 21849379, compound

HRID 862814Notes

Reaction equation

HRID 862814 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17].N1C=CC=CC=1.CN(C1C=CC=CN=1)C>ClCCl>[C:22]1([CH3:23])[CH:24]=[CH:25][C:19]([S:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:10][CH:9]=2)(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 10608380HCID 10608380, compound

Product 1

HCID 21849379HCID 21849379, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.1 g of 4-(4-butylphenyl)butanol, 1.05 g of tosyl chloride, 0.48 ml of pyridine and a catalytic amount of dimethylaminopyridine in dichloromethane was allowed to stand at room temperature overnight. The reaction mixture was poured into 50 ml of ice water and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was distilled away. The residue was purified by silica gel column chromatography (ethyl acetate:hexane: 1:6) to give 1.2814 g of 4-(4-butylphenyl)butyl p-toluenesulfonate as a colorless, oily substance.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane: 1:6)

Sources & evidence

ORD record
ord-9423cf49946e4cd190cba9d64e156680
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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