(S)-5-Oxotetrahydrofuran-2-carbonyl chloride → 2(3H)-Furanone, dihydro-5-(1-oxopropyl)-, (S)-

Temperature

-78 °C

To a solution of (2S)-5-oxotetrahydrofuran-2-carbonyl chloride (compound 28b, 70 g, 473 mmol) in dry THF (400 mL) was added ethylmagnesium bromide (173 mL, 520 mmol, 3M in THF) slowly at −78° C. under N2. After addition, the reaction mixture was stirred at −78° C. for another 2 hours. The mixture was then quenched with saturated NH4Cl solution and extracted with EtOAc (500 mL) twice. The combined organic layers were 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 35 g of (5S)-5-propanoyltetrahydrofuran-2-one (compound 28c) as a light yellow oil.

1. additionAfter addition
2. customThe mixture was then quenched with saturated NH4Cl solution
3. extractionextracted with EtOAc (500 mL) twice
4. concentrationThe combined organic layers were concentrated in vacuo
5. customthe residue was purified by column chromatography on silica gel (eluting with 1:7 to 1:3 EtOAc in petroleum ether)

ORD record

ord-04da0a1f39064ad8a97f0420d0bab13e

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09441008B2