Réaction #324434

Équation de réaction

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

DIBAL-H

→

title compound

Rendement 58.5%

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

Rendement 58.5%

Solvants

Et2O

Conditions de réaction

Traitement

1. 1
   Autrethe 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
   Autrethe 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
   Autrethe organic layer separated
8. 8
   Autredried

Mode opératoire

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