Potassium Hydroxide → 6-(4-Aminophenyl)hex-5-yn-1-ol
Reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:8][CH:7]=1)=O.[OH-].[K+]>CC(O)C>[NH2:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:10][CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of Intermediate 39 (8.5 mmol) in IPA (20 mL) was added to a 100° C. solution of potassium hydroxide (1.4 g, 26 mmol) in IPA (150 mL). The mixture was henceforth heated to reflux for 3.5 hours before being concentrated to drying under reduced pressure. The residue was partitioned between water and dichloromethane. The aqueous phase was extracted three times with dichloromethane. The combined extracts were concentrated to dryness under reduced pressure, and the resulting residue was purified via automated flash silica gel chromatography, using a 25 g Silicycle SiliSep flash column (hexanes/ethyl acetate). Concentration of the desired fractions under reduced pressure provided the title compound as a pale blond oil. ES/MS calcd. for C12H16NO+: 190.1. Found m/z=190.2 (M+H)+