Sodium Iodide → HCID 21432353, compound

HRID 2399086Notes

Reaction equation

HRID 2399086 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13]Cl)[O:6][CH2:5][CH2:4][O:3]1.[C-:15]#[N:16].[Na+].[Na+].[I-].[C-]#N.[K+]>CCO.O>[CH3:1][C:2]1([CH2:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][C:15]#[N:16])[O:6][CH2:5][CH2:4][O:3]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8929Sodium CyanideHCID 9032Potassium CyanideHCID 21432391HCID 21432391, compound

Product 1

HCID 21432353HCID 21432353, compoundYield 96.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Methyl-2-(7-chloro-3-heptynyl)-1,3-dioxolane (21.6 g, 0.1 mol) was dissolved in 120 ml EtOH (convenience; dimethylformamide, dimethylsulfoxide, or other polar solvents may be used) and added to a solution of NaCN (9.8 g, 0.2 mol) and NaI (2.0 g, 0.013 mol) in 80 ml H2O. KCN, NH4CN or other cyanide salts may be used. The reaction was concentrated to remove the solvent and was extracted with three 100 ml portions of ether. The combined organic extracts were washed with 2-50 ml portions of water and brine. After drying over anhydrous MgSO4, the solvent was removed to give 20 g of 2-methyl-2-(7-cyano-3-heptynyl)-1,3-dioxolane, pure enough to use directly in the next step. Yield: 20 g, 99%. IR (CHCl3): 3000, 2950, 2890, 2250, 1675 cm-1.

Workup

  1. concentrationThe reaction was concentrated
  2. customto remove the solvent
  3. extractionwas extracted with three 100 ml portions of ether
  4. washThe combined organic extracts were washed with 2-50 ml portions of water and brine
  5. dry with materialAfter drying over anhydrous MgSO4
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-d23437a979b948f9a85eebd3fe2ffbc7
Source dataset
uspto-grants-1977_05
Patent number
US04026911

Reaction notes

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