Reaction #9732

Reaction equation

methanol

borane

5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-carboxylic acid

→

title compound

5-(4-chlorophenyl)-3-hydroxymethyl-2-trifluoromethylfuran

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction stirred at room temperature for 2 hours
2. 2
   TemperatureThe reaction was cooled to 0° C.
3. 3
   Otherwas evaporated
4. 4
   OtherThe residue was purified by SPE (Si cartridge) sequentially using dichloromethane, chloroform and chloroform:ether (9:1) as eluents

Procedure

A mixture of 5-(4-chlorophenyl)-2-(trifluoromethyl)furan-3-carboxylic acid (0.30 g) in tetrahydrofuran (10 ml) stirred under a nitrogen atmosphere at 0° C. was treated with a 1M solution of borane in tetrahydrofuran (10.33 ml) and the reaction stirred at room temperature for 2 hours. The reaction was cooled to 0° C.; treated with methanol (4 ml) and after 15 minutes the reaction mixture was evaporated. The residue was purified by SPE (Si cartridge) sequentially using dichloromethane, chloroform and chloroform:ether (9:1) as eluents to give the title compound as a white solid.

Source