[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]#[N:20])=[CH:6][CH:5]=1)(O)=[O:2].C(N(CC)CC)C.ClC(OCC)=O.[BH4-].[Na+].Cl>O1CCCC1.O1CCCC1.O>[OH:2][CH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:19]#[N:20])=[CH:6][CH:5]=12.8 g (0.0107 mol) of 1-(4-carboxyphenyl)-2-cyanoindole was dissolved in 100 ml tetrahydrofuran and cooled in an ice-bath. 1.5 ml (0.01 mol) of triethylamine was added, followed by the dropwise addition of 1.1 ml (0.01 mol) ethyl chloroformate. After stirring for 20 minutes the precipitate was removed by filtration and a solution of 1.2 g (0.1 mol) sodium borohydride in 60 ml tetrahydrofuran-water 3:1 was added dropwise to the filtrate. After stirring an additional 20 minutes, 5 ml of 10% hydrochloric acid was added, and the mixture extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated to an oil. The oily material was chromatographed on silica gel, eluting with ethyl acetate-hexane 7:3 to give 1.5 g (0.006 mole) of 1-[4-(hydroxymethyl)phenyl]-2-cyanoindole as an oil.
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