Reaktion #89017

Reaktionsgleichung

(5S)-5-propanoyltetrahydrofuran-2-one

compound 28c

(5S)-5-propanoyltetrahydrofuran-2-one

L-selectride

→

(5S)-5-(1-hydroxypropyl)tetrahydrofuran-2-one

Ausbeute 56.3%

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   SonstigeThe reaction mixture was then quenched with 2N HCl (200 mL)
3. 3
   Extraktionextracted with EtOAc (400 mL) twice
4. 4
   WaschenThe combined organic layers were washed with brine (100 mL)
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigethe residue was purified by column chromatography on silica gel (eluting with 1:7 to 1:3 EtOAc in petroleum ether)

Vorschrift

To a solution of (5S)-5-propanoyltetrahydrofuran-2-one (compound 28c, 35 g, 246.5 mmol) was added L-selectride (320 mL, 320 mmol, 1 M in THF) at −78° C. under N2. After addition, the reaction mixture was stirred at −78° C. for 2 hours. The reaction mixture was then quenched with 2N HCl (200 mL) and extracted with EtOAc (400 mL) twice. The combined organic layers were washed with brine (100 mL), concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:7 to 1:3 EtOAc in petroleum ether) to afford 20 g of (5S)-5-(1-hydroxypropyl)tetrahydrofuran-2-one (compound 28d) as a yellow oil. (Refer to Eur. J. Med. Chem. 1997, 32, 617-623).

Quelle