Reaction #324434

Reaction equation

5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester

DIBAL-H

→

title compound

Yield 58.5%

(5-Methyl-2-trifluoromethyl-furan-3-yl)-methanol

Yield 58.5%

Solvents

Et2O

Conditions

Workup

1. 1
   Otherthe ice bath was removed
2. 2
   workup.ADDITIONadditional DIBAL-H was added (1.0 M in THF, 14.5 mL)
3. 3
   workup.WAITAfter 2 h
4. 4
   Otherthe reaction was quenched with a saturated solution of sodium potassium tartrate (aq.)
5. 5
   workup.WAITAfter 18 h
6. 6
   workup.ADDITIONEtOAc was added
7. 7
   Otherthe organic layer separated
8. 8
   Otherdried

Procedure

To a solution of 5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester (0.83 g, 3.7 mmol) in Et2O at 0° C., was added DIBAL-H (1.0 M in THF, 1.5 mL). After 10 min, the ice bath was removed and additional DIBAL-H was added (1.0 M in THF, 14.5 mL). After 2 h, the reaction was quenched with a saturated solution of sodium potassium tartrate (aq.) and allowed to stir overnight. After 18 h, EtOAc was added and the organic layer separated and dried provide the title compound (0.39 g, 58%). 1H NMR (CDCl3): 6.19 (s, 1H), 4.62 (s, 2H), 2.36-2.28 (m, 3H).

Source