Acetonitrile → (5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) acetonitrile

HRID 612735Notes

Reaction equation

HRID 612735 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14]Br)[CH:5]=[CH:4][C:3]1=2.CCOC(C)=O.[C:23](#[N:25])C>[C-]#N.C([N+](CC)(CC)CC)C>[CH3:1][C:2]1([CH3:16])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH2:14][C:23]#[N:25])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 27355976-(Bromomethyl)-1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydronaphthalene

Product 1

HCID 18177926(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) acetonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 3014735Tetraethylammonium cyanideCatalyst

Procedure

To a solution of (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) bromomethane (21) (100 mg, 0.44 mmol) in acetonitrile (2 mL) was added tetraethylammonium cyanide (83 mg, 0.53 mmol). The resulting golden yellow solution was stirred at rt overnight. The solvent was removed in vacuo and to give a residue that was subjected to chromatograpy (10% EtOAc/90% hexane) to give 59 mg (78%) of (5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl) acetonitrile (22). 1H NMR (400 MHz, CDCl3) δ7.31 (d, J=8.2 Hz, 1H, aromatic), 7.23 (d, J=1.8 Hz, 1H, aromatic), 7.08 (dd, J=8.0 and 1.8 Hz, 1H, aromatic), 3.69 (s, 2H, CH2), 1.69 (s, 4H, 2CH2), 1.28 (s, 6H, 2CH3), (s, 6H, 2CH3).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a residue that

Sources & evidence

ORD record
ord-4b26621781d34666b8fa0406b0e03f57
Source dataset
uspto-grants-1999_12
Patent number
US06005007

Reaction notes

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