Sodium Cyanide → HCID 178455453, compound

Participants

Reaction Conditions

Reaction Steps

38.2 g of crude trans-methanesulfonic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexylmethyl ester and 16.7 g (340 mmol, 3.2 eq) of sodium cyanide dissolved in 380 mL of DMF were stirred at 80° C. for 2 h. After cooling the reaction mixture down to RT, it was partitioned between ether and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed on silica gel with a 9:1 v/v mixture of n-hexane and EtOAc as the eluent giving 24.2 g (80% over two steps) of pure trans-[4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-acetonitrile as colorless viscous oil, MS: 290 (MNa+).

Provenance & Evidence