[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:15])=[C:9]([CH2:12][CH:13]=[CH2:14])[CH:10]=2)[CH2:5][C:4]1=[O:16])[CH3:2].C([O-])(=O)C.[OH-].[Na+].[BH4-].[Na+]>C(OCC)C.O.O1CCCC1>[CH3:14][CH:13]1[O:15][C:8]2=[CH:7][C:6]3[CH2:5][C:4](=[O:16])[N:3]([CH2:1][CH3:2])[C:11]=3[CH:10]=[C:9]2[CH2:12]1
To a solution of 6.0 g. (27.6 mmoles) of 1-ethyl-5-hydroxy-6-allyloxindole in 105 ml. of tetrahydrofuran was added 8.79 g. (27.6 mmoles) of mecuric acetate, and the reaction stirred for 1.5 hours. The mixture was diluted with 29 ml. of 3N sodium hydroxide solution followed by the addition of 522 mg. (13.7 mmoles) of sodium borohydride in 29 ml. of 3N sodium hydroxide solution. The mixture was stirred for 1 hour and was then diluted with diethyl ether and water. The organic phase was washed with water and a saturated brine solution, and then dried over magnesium sulfate. Evaporation of the solvent and chromatographing of the residue on 100 g. of silica gel, using diethyl ether-hexane (1:1, v:v) as the eluent, gave 1.68 g. (28% yield) of the desired product.
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