Pyridine → 1-Methanesulfonyloxy-2,2,5,5-tetramethylcyclopentane

HRID 231719

Reaction equation

HRID 231719 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].N1C=CC=CC=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:17][S:18]([O:9][CH:3]1[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]1([CH3:10])[CH3:1])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 5516962,2,5,5-Tetramethylcyclopentan-1-ol

Product 1

HCID 137823751-Methanesulfonyloxy-2,2,5,5-tetramethylcyclopentaneYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.84 g of 2,2,5,5-tetramethylcyclopentanol and 3.2 ml of pyridine were dissolved in 20 ml of methylene chloride, and 4.5 g of methanesulfonyl chloride was added thereto. The mixture was stirred at room temperature for 12 hours, and then 50 ml of aqueous saturated sodium hydrogen carbonate solution was added thereto. The mixture was extracted with 50 ml of ethyl acetate, and the organic layer was washed with aqueous 10% copper sulfate solution, and concentrated under reduced pressure. The resulting residue was recrystallized from n-hexane, whereby 1.26 g of 1-methanesulfonyloxy-2,2,5,5-tetramethylcyclopentane was obtained (m.p. 46° C.).

Workup

  1. extractionThe mixture was extracted with 50 ml of ethyl acetate
  2. washthe organic layer was washed with aqueous 10% copper sulfate solution
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-6c09d014ffb9417a824fddb49fd9c689
Source dataset
uspto-grants-1989_07
Patent number
US04847390

Linked notes

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