Hydrochloric Acid → HCID 12914878, compound

HRID 979161Notes

Reaction equation

HRID 979161 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=O)[CH2:3][CH2:2]1.C1(C)C=CC=CC=1.O=P(Cl)(Cl)Cl.Cl.C[Si]([C:29]#[N:30])(C)C>N1C=CC=CC=1>[C:29]([C:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][CH:3]=1)#[N:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 68110ChromanoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 12914878HCID 12914878, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Eleven grams 2H-[1]benzopyran-4-one are dissolved in 33 ml 2.5M trimethylsilyl cyanide (CH2Cl2). After addition of 50 mg Znl2, the mixture is stirred 12 h. Then 30 ml toluene, 115 ml pyridine and 21 ml POCl3 are added and the mixture refluxed for 4 h. On cooling, it is poured into 1000 ml 5% HCl and extracted with four 100 ml portions of ether. The extracts dried over Na2SO4, filtered, concentrated under reduced pressure and vacuum distilled (bulb-to-bulb, oven temperature 150°) to yield 4-cyano-2H[1]benzopyran.

Workup

  1. additionAfter addition of 50 mg Znl2
  2. temperaturethe mixture refluxed for 4 h
  3. temperatureOn cooling
  4. extractionextracted with four 100 ml portions of ether
  5. dry with materialThe extracts dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure and vacuum
  8. distillationdistilled (bulb-to-bulb, oven temperature 150°)

Sources & evidence

ORD record
ord-7f6a3e72499b4e569f7619189df6abf9
Source dataset
uspto-grants-1987_05
Patent number
US04666916

Reaction notes

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