Potassium Cyanide → HCID 19376174, compound

HRID 1885362Notes

Reaction equation

HRID 1885362 reaction equation
I[CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:8]([I:13])[C:9]=2[OH:12])[O:4][C:3]1([CH3:20])[CH3:19].[C-:21]#[N:22].[K+]>C(O)C>[C:21]([CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:8]([I:13])[C:9]=2[OH:12])[O:4][C:3]1([CH3:20])[CH3:19])#[N:22]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 21649714HCID 21649714, compound

Product 1

HCID 19376174HCID 19376174, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,6-Diiodo-2,2-dimethyl-5-hydroxy-7-pent-1-yl chromane (0.293 g) and potassium cyanide (50 mg) were dissolved in 15 ml absolute ethanol and heated to reflux. After 4.5 hours, the reaction was allowed to cool to room temperature. The solvent was removed in vacuo. Water was added and extracted with methylene chloride. The methylene chloride was removed in vacuo. The residue was chromatographed on a silica gel column eluted with chloroform (TLC Rf=0.2, chloroform). The appropriate fractions were combined to yield 51 mg of product.

Workup

  1. temperatureheated to reflux
  2. customThe solvent was removed in vacuo
  3. additionWater was added
  4. extractionextracted with methylene chloride
  5. customThe methylene chloride was removed in vacuo
  6. customThe residue was chromatographed on a silica gel column
  7. washeluted with chloroform (TLC Rf=0.2, chloroform)

Sources & evidence

ORD record
ord-19f84a0bf2834b328633c738f2930fd1
Source dataset
uspto-grants-1992_09
Patent number
US05144030

Reaction notes

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