1-Methyl-1H-indole-4-carbaldehyde → alpha-(2-methoxyphenyl)-1-methyl-1H-indol-4-methanol
Reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([CH:11]=[O:12])[C:5]=2[CH:4]=[CH:3]1.[Mg].Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22]>O1CCCC1>[CH3:22][O:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH:11]([C:6]1[C:5]2[CH:4]=[CH:3][N:2]([CH3:1])[C:10]=2[CH:9]=[CH:8][CH:7]=1)[OH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Using the procedure of Step B of Example 1, 36.8 g of the product of Step A and 104 ml of a solution of 2-bromo anisole magnesium compound in tetrahydrofuran titrating 1.94N were reacted. Extraction was carried out with ethyl acetate and the extracts were washed with salt water and brought to dryness. The residue was chromatographed on silica (eluant: methylene chloride) to obtain 46.5 g of the expected product melting at 95° C.