Methanol → Indole
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C([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2C(C)C)=[CH:7][CH:6]=1)(OC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.[OH-].[Na+]>O1CCCC1>[NH:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][CH:13]=2)[CH:9]=[CH:10]1C([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2C(C)C)=[CH:7][CH:6]=1)(OC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.[OH-].[Na+]>O1CCCC1>[NH:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][CH:13]=2)[CH:9]=[CH:10]1A solution of 0.250 g (1.15 mmole) of 6-carbomethoxy-1-(2-propyl)indole in 2 mL of anhydrous tetrahydrofuran was added dropwise to a stirring slurry of lithium aluminum hydride (52.4 ing 1.38 mmole) in 7 mL of anhydrous tetrahydrofuran under argon it 0° C. and then stirred at 25° C. for 45 min. The solution was cooled to 0° C. and 0.340 mL of methanol was added dropwise, followed by 0.58 mL of 1N sodium hydroxide solution. The slurry was stirred at 25° C. for 15 min. The white precipitate was filtered through celite, and the solution concentrated. The residue was suspended in 20 mL of ethyl acetate and 20 mL of water. The layers were separated. The aqueous layer was back-extracted with ethyl acetate and both ethyl acetate layers were combined and dried over magnesium sulfate. Concentration gave 6-hydroxymethyl-1-(2-prol:)yl)indole as an oil (214 mg).
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