Lithium hydroxide, monohydrate → 2-(7-Cyano-1H-indol-1-yl)acetic acid

反応式

O[Li].O.[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[N:13]([CH2:15][C:16]([O:18]CC)=[O:17])[CH:12]=[CH:11]2)#[N:5]>O.C1COCC1>[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[N:13]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:11]2)#[N:5]

参加物

実験手順

A solution of LiOH.H2O (1.4 g, 34.06 mmol, 3.0 equiv.) in water (10 ml) was added at 0° C. to a solution of ethyl 2-(7-cyano-1H-indol-1-yl)acetate (2.6 g, 11.37 mmol, 1.0 equiv.) in THF, and the mixture was stirred for 2 h at RT. When the reaction was complete (TLC monitoring), the mixture was concentrated under vacuum and the residue was taken up in water (50 ml). Extraction with ethyl acetate (50 ml) was carried out, and then the aqueous phase was adjusted to pH≈3-4 with 10% HCl solution. Extraction with DCM (2×50 ml) was then carried out, and the combined organic phases were washed with sat. NaCl solution, dried over Na2SO4 and concentrated under vacuum. The desired product was isolated in the form of a light-yellow solid.