Pyridine → HCID 22858125, compound

HRID 1608757Notes

Reaction equation

HRID 1608757 reaction equation
[OH:1][CH2:2][C@H:3]([C:5]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:4].N1C=CC=CC=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl.S([O-])([O-])(=O)=O.[Cu+2]>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:1][CH2:2][C@H:3]([C:5]2([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6]2)[CH3:4])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 22852127HCID 22852127, compound

Product 1

HCID 22858125HCID 22858125, compoundYield 169.5%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3a (1.79 g, 12.4 mmol) , pyridine (5 mL), and p-toluenesulfonyl chloride (4.26 g, 22.3 mmol) in dichloromethane (40 mL) was stirred below 10° C. for 2 days. The reaction mixture was poured into copper (II) sulfate solution and extracted with diethyl ether. The combined organic layers were washed with copper (II) sulfate solution, water, sodium bicarbonate solution and brine, and dried over sodium sulfate. Filtration and concentration gave 6.27 g of an oily material, which was purified by column chromatography (silica gel 60 g, ethyl acetate in n-hexane, 5-33%) to give 3.74 g (quantitative) of 4a as a colorless oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic layers were washed with copper (II) sulfate solution, water, sodium bicarbonate solution and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-9fd9f82a53e44a28848a233fae35c176
Source dataset
uspto-grants-1995_03
Patent number
US05397775

Reaction notes

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