Trimethylsilyl cyanide → 7-Methoxy-4-cyano chrom-3-ene

HRID 847213Notes

Reaction equation

HRID 847213 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[CH2:8][CH2:9][O:10]2)=[CH:5][CH:4]=1.C[Si]([C:18]#[N:19])(C)C>[Zn+2].[I-].[I-].CC#N>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:18]#[N:19])=[CH:8][CH2:9][O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 43875107-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Product 1

HCID 150232277-Methoxy-4-cyano chrom-3-ene

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6342AcetonitrileSolvent

Procedure

7-Methoxy-4-chromanone (7 g) was added to trimethylsilyl cyanide (TMSCN) (7 ml), CH3CN (10 ml) and a catalytic amount of ZnI2 and refluxed for 2 hrs. The reaction was cooled, evaporated to dryness, then isopropyl alcohol saturated with HCl(g) (100 ml) was added and this solution refluxed 2 hrs. The reaction was cooled, evaporated to dryness, and saturated aqueous NaCl added. This was then extracted with CH2Cl2, the organic layer separated, dried (Na2SO4), filtered and evaporated affording 7.1 of product. IR(CHCl3): 2218 cm-1.

Workup

  1. temperatureThe reaction was cooled
  2. customevaporated to dryness
  3. additionisopropyl alcohol saturated with HCl(g) (100 ml) was added
  4. temperaturethis solution refluxed 2 hrs
  5. temperatureThe reaction was cooled
  6. customevaporated to dryness, and saturated aqueous NaCl
  7. additionadded
  8. extractionThis was then extracted with CH2Cl2
  9. customthe organic layer separated
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated
  13. customaffording 7.1 of product

Sources & evidence

ORD record
ord-2f06263990ee488496d51c1ee94c1194
Source dataset
uspto-grants-1992_08
Patent number
US05140039

Reaction notes

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