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

HRID 1589589Notes

Reaction equation

HRID 1589589 reaction equation
S(Cl)(Cl)=O.N1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[CH2:6]=[C:7]1[C:8]([CH3:9])([CH3:7])[CH2:10][CH2:9][C:8]1([CH3:10])[CH3:6]

Participants

3

Reactant 2

HCID 1049PyridineHCID 24386Thionyl Chloride

Product 1

HCID 140288511-Methylene-2,2,5,5-tetramethylcyclopentane

Conditions

Temperature
0 °C

Procedure

The crude product from Part B (30 g) was dissolved in pyridine (150 ml), the solution cooled to 0° C. and treated (dropwise) with thionyl chloride (20 ml, 0.28 mole), maintaining a temperature of <5° C. The reaction mixture was stirred overnight, filtered and ether and water added. The phases were separated and the organic phase washed with water (2×200 ml) and dried (Na2SO4). The solvent was evaporated under reduced pressure to give 1-methylene-2,2,5,5-tetramethylcyclopentane (10.8 g) which was pure by GC.

Workup

  1. temperaturemaintaining a temperature of <5° C
  2. filtrationfiltered
  3. additionether and water added
  4. customThe phases were separated
  5. washthe organic phase washed with water (2×200 ml)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-91d1a64c19304d799c9ca198e55355c3
Source dataset
uspto-grants-1986_02
Patent number
US04571345

Reaction notes

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