Acetic Acid → Ethyl [2-methyl-4-({[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)phenoxy]acetate
Reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1)=O.[F:17][C:18]([F:33])([F:32])[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH2:31])[CH:26]=2)=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH3:16][C:5]1[CH:4]=[C:3]([CH2:1][NH:31][C:27]2[CH:26]=[C:25]([C:22]3[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:32])[F:33])=[CH:20][CH:21]=3)[CH:30]=[CH:29][CH:28]=2)[CH:15]=[CH:14][C:6]=1[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of ethyl (4-formyl-2-methylphenoxy)acetate (0.2 g, 0.9 mmol) in anhydrous CH2Cl2 (8 mL) was added 4′-(trifluoromethyl)-1,1′-biphenyl-3-ylamine (0.214 g, 0.9 mmol). The resulting mixture was stirred under nitrogen at room temperature for 15 mins, prior to addition of sodium triacetoxyborohydride (0.267 g, 1.26 mmol) and acetic acid (0.052 mL, 0.9 mmol). The resultant mixture was stirred for 18 h prior to quenching by cautious addition of sat. sodium bicarbonate solution (20 mL) the reaction mixture was then extracted CH2Cl2 (20 mL). The organic extract separated by hydrophobic frit and the solvent removed in vacuo. Purification by Biotage™ chromatography (Silica, 40 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (0.342 g).
Workup
- customto quenching by cautious addition of sat. sodium bicarbonate solution (20 mL) the reaction mixture
- extractionThe organic extract
- customseparated by hydrophobic frit
- customthe solvent removed in vacuo
- customPurification by Biotage™ chromatography (Silica, 40 g)
- washeluting 9:1 cyclohexane
Sources & evidence
- ORD record
- ord-4c6068d9093c47a6a4fe3a221c55ad1d
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07199239B2
Reaction notes
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