Pyridine → HCID 54082424, compound

HRID 461983Notes

Reaction equation

HRID 461983 reaction equation
O[CH:2]([CH:5]1[CH2:10][CH2:9][CH:8]2[CH:6]1[CH2:7]2)[C:3]#[N:4].N1C=CC=CC=1.S(Cl)(Cl)=O>O>[C:3]([CH:2]=[C:5]1[CH2:10][CH2:9][CH:8]2[CH:6]1[CH2:7]2)#[N:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl Chloride2×HCID 21392664HCID 21392664, compound

Product 1

HCID 54082424HCID 54082424, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.078 Mole of 2-hydroxy-2-(bicyclo[3.1.0]hex-2-yl)acetonitrile is dissolved in 200 ml. of anhydrous pyridine under nitrogen, and cooled to -50° C. 0.0942 Mole of thionyl chloride is added dropwise and the mixture allowed to warm to room temperature and then recooled to 0° C. Excess thionyl chloride is then decomposed by the addition of 2 ml. of water. The pyridine is removed by evaporation under vacuum and the resulting residue dissolved in 300 ml. of ethyl acetate. The ethyl acetate solution is then washed twice with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate is evaporated to dryness, under vacuum, and the resulting residue is chromatographed with silica gel eluting with 10% ethyl acetate-90%, vol., hexane, affording 2-(cyanomethylene)bicyclo[3.1.0]hexane.

Workup

  1. customrecooled to 0° C
  2. customThe pyridine is removed by evaporation under vacuum
  3. dissolutionthe resulting residue dissolved in 300 ml
  4. washThe ethyl acetate solution is then washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe filtrate is evaporated to dryness, under vacuum
  8. customthe resulting residue is chromatographed with silica gel eluting with 10% ethyl acetate-90%, vol., hexane

Sources & evidence

ORD record
ord-f5ab3ef3649249dc9dd331fa68639469
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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