5-Methoxytetralone → HCID 67933782, compound

HRID 979802Notes

Reaction equation

HRID 979802 reaction equation
C[Si]([C:5]#[N:6])(C)C.[Cl-].[Cl-].[Cl-].[Al+3].[CH3:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH2:17][C:18]2=O>C1(C)C=CC=CC=1>[C:5]([CH2:11][O:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH2:15][CH2:16][CH:17]=[CH:18]2)#[N:6]

Participants

5

Reactant 3

HCID 366205-MethoxytetraloneHCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67933782HCID 67933782, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Trimethylsilyl cyanide (28.2 g) and a catalytic amount of aluminum trichloride was added to a toluene solution of 5-methoxy-1-tetralone (25 g) and the reaction heated for 2 hours. The solution was evaporated to dryness. Pyridine (100 ml) was then added, followed by dropwise addition of phosphorous oxychloride (40 ml). Upon complete addition the reaction was heated to 120° C. for 2 hours. The reaction was cooled and poured onto ice containing aqueous hydrochloric acid. The mixture was extracted with ether (100 ml). The organic layer was separated, dried, filtered and evaporated affording the desired product as an oil which solidified upon standing.

Workup

  1. temperaturethe reaction heated for 2 hours
  2. customThe solution was evaporated to dryness
  3. additionPyridine (100 ml) was then added
  4. additionfollowed by dropwise addition of phosphorous oxychloride (40 ml)
  5. additionUpon complete addition the reaction
  6. temperatureThe reaction was cooled
  7. additionpoured onto ice containing aqueous hydrochloric acid
  8. extractionThe mixture was extracted with ether (100 ml)
  9. customThe organic layer was separated
  10. customdried
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-f6e85a7a75b74c1fb503e6d4bf54c5c6
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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