Reaction #56210

Reaction equation

α-cyano-4-fluoro-3-phenoxybenzyl alcohol

2-(2-benzothienyl)-3-methylbutanoic acid

N,N'-dicyclohexylcarbodiimide

→

α-cyano-4-fluoro-3-phenoxybenzyl 2-(2-benzothienyl)-3-methylbutanoate

Solvents

methylene chloride

dimethylformamide

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   Extractionextracted with water
3. 3
   ExtractionThe aqueous phase is extracted with ether
4. 4
   WashThe combined organic phases are washed with saturated aqueous sodiun bicarbonate, water and saturated aqueous sodium chloride
5. 5
   Dryingdried over calcium sulfate and solvent
6. 6
   Otherevaporated

Procedure

To a stirred solution of α-cyano-4-fluoro-3-phenoxybenzyl alcohol (437 mg, 1.8 mmol), 2-(2-benzothienyl)-3-methylbutanoic acid (2.0 mmol) and 4-dimethylaminopyridine (0.65 mmol) in 20 ml of methylene chloride and 2 ml of dimethylformamide is added N,N'-dicyclohexylcarbodiimide (2.0 mmol). The reaction mixture is stirred, under nitrogen, for two hours and then filtered and extracted with water. The aqueous phase is extracted with ether. The combined organic phases are washed with saturated aqueous sodiun bicarbonate, water and saturated aqueous sodium chloride, dried over calcium sulfate and solvent evaporated to give α-cyano-4-fluoro-3-phenoxybenzyl 2-(2-benzothienyl)-3-methylbutanoate.

Source