Chloride → HCID 13409052, compound

Participants

Reaction Steps

To a suspension of the compound from Example 25, (20.9 g., 0.067 mole) in 125 ml. of absolute ethanol was added 0.79 g. (0.021 mole) of NaBH4. The mixture was stirred for 20 minutes at room temperature. The reaction mixture was diluted by careful addition of water and was then acidified with dilute HCl. The ethanol was evaporated under reduced pressure and the aqueous residue was extracted with methylene chloride. The organic solution was washed with brine, dried over Na2SO4 and evaporated to provide 20 g. of benzylic alcohol. This alcohol (20 g., 0.064 mole) was dissolved in 150 ml. of chloroform and 18.7 ml. of thionyl chloride was added. After the solution had been stirred for 5 hours at room temperature, the solvent was evaporated to give 21.1 g. of benzylic chloride. NMR (CDCl3): 4.70 (2H, s, ArCH2Cl). This chloride (21.1 g., 0.064 mole) was dissolved in 150 ml. of 95% ethanol and a solution of NaCN (3.74 g., 0.076 mole) in 25 ml. of water was added. The mixture was refluxed for 8 hours. The ethanol was evaporated and the aqueous residue was extracted with methylene chloride. The organic extract was washed with brine, dried over Na2SO4 and evaporated. The crude product was quickly passed through a short silica gel column using methylene chloride as the solvent. The desired product (16.6 g.) was obtained as a yellow solid. NMR (CDCl3): 3.93 (2H, s, ArCH2CN); IR (CHCl3) 2250 cm-1.

Provenance & Evidence