Pyridine → HCID 19045537, compound

HRID 1591219Notes

Reaction equation

HRID 1591219 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:8])[CH3:7].N1C=CC=CC=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH3:16][S:17]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:8])[CH3:7])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 114236171,6-Heptanediol

Product 1

HCID 19045537HCID 19045537, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(±)-Heptan-1,6-diol (1.06 g, 8 mmol) and pyridine (1.36 ml, 1.33 g, 16.8 mmol) were dissolved in dichloromethane (20 ml) and the mixture was cooled in ice. Methanesulfonyl chloride (0.65 ml, 0.96 g, 8.4 mmol) was added dropwise and the mixture was stirred at room temperature for 18 hours. Dichloromethane (50 ml) was added and the mixture was washed with aqueous HCl (1M, 50 ml) and brine (30 ml), dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/20% hexane, to give the alcohol as an oil (1.01 g, 60%).

Workup

  1. temperaturethe mixture was cooled in ice
  2. washthe mixture was washed with aqueous HCl (1M, 50 ml) and brine (30 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with EtOAc/20% hexane

Sources & evidence

ORD record
ord-d51ce0113ae04fb5a7097b9ef3ced9e7
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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