Trimethylsilyl cyanide → HCID 86741182, compound

HRID 979800Notes

Reaction equation

HRID 979800 reaction equation
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[Cl-].[Al+3].[Cl-].[Cl-].C[Si]([C:24]#[N:25])(C)C>C1C=CC=CC=1>[C:24]([CH2:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]=[CH:8]2)#[N:25]

Participants

5

Reactant 3

HCID 82115Trimethylsilyl cyanideHCID 6451240Aluminum(III) ChlorideHCID 82192465,6-dimethoxy-1-tetralone

Product 1

HCID 86741182HCID 86741182, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

5,6-dimethoxytetralone (20 g) was dissolved in benzene (20 ml) and trimethylsilyl cyanide (16 ml). A catalytic amount of aluminum chloride was added and the reaction heated at 70° C. under nitrogen for 30 minutes. The volatiles were removed in vacuo and methanol (20 ml) added. Gaseous hydrochloric acid was bubbled through the methanol solution for 30 minutes resulting in precipitation of a solid. Stirring was continued for 1 hour, then the mixture was filtered and dried affording 19.9 g. of product (96% yield); m.p. 138°-9° C.

Workup

  1. customThe volatiles were removed in vacuo and methanol (20 ml)
  2. additionadded
  3. customGaseous hydrochloric acid was bubbled through the methanol solution for 30 minutes
  4. customresulting in precipitation of a solid
  5. filtrationthe mixture was filtered
  6. customdried
  7. customaffording 19.9 g

Sources & evidence

ORD record
ord-288484d9dbb34f1cbfe76439061ad0e6
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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