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

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

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.