1-Tetralone → 1-Trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydronaphthalene

HRID 467038

Reaction equation

HRID 467038 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C-:12]#[N:13].[Li+].[CH3:15][Si:16](C#N)([CH3:18])[CH3:17]>C1COCC1>[C:12]([C:1]1([O:11][Si:16]([CH3:18])([CH3:17])[CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)#[N:13]

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 75478Lithium cyanideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 117469071-Trimethylsilyloxy-1-cyano-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,3,4-tetrahydronaphthalene-1-one (20 g, 140 mmol) in THF (150 mL) was added 6 mL of a 0.5M solution of lithium cyanide (3 mmol, 0.02 equivalent). The reaction mixture was stirred for ~2 minutes and then trimethylsilyl cyanide (25 g, 250 mmol, 1.8 equivalent) was added in one portion. The reaction mixture was stirred for 4.5 hours. Solvents and excess trimethylsilyl cyanide were removed under reduced pressure to give the title compound as a yellow oil. The oil was used in the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred for 4.5 hours
  2. customSolvents and excess trimethylsilyl cyanide were removed under reduced pressure

Sources & evidence

ORD record
ord-346b244cc9ba41798e732c5fa26a656b
Source dataset
uspto-grants-1992_10
Patent number
US05158948

Linked notes

Loading…