Réaction #7102

Équation de réaction

3,3-dimethylglutaric anhydride

lithium aluminum hydride

water

sodium hydroxide

water

→

3,3-dimethyl-1,5-pentanediol

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was then brought gradually up-to reflux
2. 2
   Températurethe mixture was cooled
3. 3
   FiltrationThe mixture was then filtered
4. 4
   Extractionthe precipitate extracted with EtOAc (×3)
5. 5
   Autrethe combined organics evaporated

Mode opératoire

A solution of 3,3-dimethylglutaric anhydride in dry THF (60 cm3) was added over 30 min. to lithium aluminum hydride in dry THF (300 cm3) under nitrogen at 0° C. The mixture was then brought gradually up-to reflux. After 3 h, the mixture was cooled, treated with water (3.3 cm3), sodium hydroxide solution (15%, 3.3 cm3) and water (9.9 cm3). The mixture was then filtered, the precipitate extracted with EtOAc (×3), and the combined organics evaporated to afford 3,3-dimethyl-1,5-pentanediol (quantitative yield); 1H NMR (CDCl3) δ 0.95 (s, 6H), 1.57 (t, 4H, J=6.3 Hz), 3.75 (t, 4H, J=6.3 Hz).

Source