Ammonium Chloride → HCID 19390053, compound

Participants

Reaction Steps

Sodium borohydride (0.110 g) was added, at 0° C. and under nitrogen atmosphere, to a solution of 1.35 g of 9-acetoxy-3-formyl-spiro[5.5]undecane (IV) in 50 ml of methanol. After 2 hrs, 10 ml. of a saturated aqueous ammonium chloride solution were added and the resulting mixture evaporated under reduced pressure. The residue, dissolved in 150 ml. of ethyl acetate, was washed with water to neutral pH; the organic layer, dried over anhydrous sodium sulfate, was evaporated under reduced pressure to give 1.50 g of 9-hydroxymethyl-3-acetoxy-spiro[5.5]undecane used as such in the following step. TLC: Rf=0.35 (SiO2 plates, diethylether/n-hexane 55/45). 1H-NMR (300 MHz, CDCl3, ppm from TMS): 4.73 (1H, hept), 3.47 (2H, d), 2.03 (3H, s) 1.90-0.95 (17H, m).

Provenance & Evidence