Sodium Hydroxide → HCID 15790542, compound

Participants

Reaction Steps

A solution of 2.4 g (0.009 moles) of the product obtained from Step B and 20 mL of toluene was added with stirring to a mixture of 1.8 g (0.010 moles) of triethylphosphite, 0.1 g (0.0004 moles) of benzyltriethyl ammonium chloride, 100 mL of toluene and 50 mL of 50% aqueous sodium hydroxide solution. A steady stream of air was introduced into the vigorously stirred reaction mixture at room temperature for 1 hour. The resulting mixture was partitioned between 100 mL of Et2O and 200 mL of water and the aqueous layer was extracted with two 100 mL portions of Et2O. The combined organic layers were washed twice with 100 mL of water, twice with saturated aqueous sodium bisulfite solution, dried over MgSO4 and concentrated. The resulting crude product was chromatographed on silica gel using 2:1 hexanes-ethyl acetate to give 1.2 g of an oil that solidified on standing.

Provenance & Evidence