Reaction #89017

Reaction equation

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

compound 28c

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

L-selectride

→

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

Yield 56.3%

Conditions

Workup

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

Procedure

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).

Source