Trimethylsilyl cyanide → 5,6-Dimethoxy-3,4-dihydronaphthalene-1-carbonitrile

HRID 2290903Notes

Reaction equation

HRID 2290903 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.C[Si]([C:20]#[N:21])(C)C.[Al+3].[Cl-].[Cl-].[Cl-]>C1C=CC=CC=1>[C:20]([C:8]1[C:9]2[C:4](=[C:3]([O:2][CH3:1])[C:12]([O:13][CH3:14])=[CH:11][CH:10]=2)[CH2:5][CH2:6][CH:7]=1)#[N:21]

Participants

5

Reactant 3

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

Product 1

HCID 135385495,6-Dimethoxy-3,4-dihydronaphthalene-1-carbonitrileYield 96.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 5,6-dimethoxy-1-tetralone (30 g, 0.14 mole), trimethylsilylcyanide (15.8 g, 0.156 mole), ca. 15 mLs dry benzene, and catalytic AlCl3 was stirred under N2 at 70° (oil bath) for 15 hours. Benzene was removed (in-vacuo), 300 mL MeOH was added to the crude product, and the solution was stirred at 0°-10° C. as HCl was bubbled through the solution for 3 hours. Methanol was evaporated (in-vacuo) and ca. 500 mL water was added to the residue. The resultant solid was filtered, washed with water, and dried (under high-vacuum) to yield 29.2 g of yellow solid. (99.8%); M+ 215; mp 139°-40° C.

Workup

  1. customBenzene was removed (in-vacuo), 300 mL MeOH
  2. additionwas added to the crude product
  3. customwas bubbled through the solution for 3 hours
  4. customMethanol was evaporated (in-vacuo) and ca. 500 mL water
  5. additionwas added to the residue
  6. filtrationThe resultant solid was filtered
  7. washwashed with water
  8. customdried (under high-vacuum)

Sources & evidence

ORD record
ord-21df0d002e594ac185623155eddbf22c
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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