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

HRID 1534528Notes

Reaction equation

HRID 1534528 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>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

4

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 1

HCID 6342AcetonitrileSolvent

Procedure

7-Methoxy-4-chromanone (7 g) was added to trimethylsilyl cyanide (TMSCN) (7 ml), CH3CN (10 ml) and a catalytic amount of ZnIhd 2 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 g of product IR(CHCl3) 2218 cm-1 :

Workup

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

Sources & evidence

ORD record
ord-92a786095dcd44c5a31c3878f1a2a926
Source dataset
uspto-grants-1992_02
Patent number
US05089519

Reaction notes

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