Sodium Hydroxide → HCID 77324662, compound

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Reaction Steps

To 1.60 g of product from Example 1, Step C, under argon, is added 22 ml of 2.5N sodium hydroxide. The reaction mixture is heated to its reflux temperature and maintained at this temperature for 20 hours. The gum that is originally present dissolves and the solution turns a dark brown. The reaction mixture is evaporated in vacuo and the residue treated with ethyl alcohol. The solids are isolated by filtration, rinsed with ethyl alcohol and diethyl ether and air dried briefly. The resulting solid is dissolved in water and loaded onto a column of XAD-4 resin (previously washed with 1 liter of 50:50 methyl alcohol:water, followed by 500 ml of water). The column is eluted with 1 liter of water followed by 1 liter of methyl alcohol. The methyl alcohol fractions containing the Rf 0.60 component (7:1 water:methyl alcohol; reverse phase tlc plates) are combined, evaporated in vacuo and the residue is triturated with ethyl alcohol. The solids are collected, rinsed with ethyl alcohol and air dried to give 0.86 g of the desired product as a light brown solid. 1H NMR(D2O): δ2.79(m,2H); 3.01(m,2H); 3.21(m,2H); 3.79(m,1H); methine next to OH approx. 4.86; 6.77(s,2H,Ar); 7.3-7.5(m,4H,Ar).

Provenance & Evidence