Methanol → HCID 12115479, compound

Reaction equation

[Na].[CH3:2][CH:3]([C:8]1[CH:14]=[C:13]([C:15](F)([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:9]=1[NH2:10])[CH2:4][CH:5]([CH3:7])[CH3:6].[CH3:25][OH:26]>>[CH3:2][CH:3]([C:8]1[CH:14]=[C:13]([C:15]([O:26][CH3:25])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:11][C:9]=1[NH2:10])[CH2:4][CH:5]([CH3:7])[CH3:6]

Participants

Reactant 3

HCID 887Methanol

HCID 5360545Sodium

HCID 22734601HCID 22734601, compound

Product 1

HCID 12115479HCID 12115479, compoundYield 87%

Procedure

Sodium (533 mg, 23 mmol) was dissolved in methanol (40 ml), followed by adding thereto 2-(1,3-dimethylbutyl)-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (2 g, 5.8 mmol), and the resulting mixture was stirred at reflux temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulfate and then concentrated under reduced pressure, and the resulting residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain 1.8 g of the desired compound.