Tetrahydrofuran → Tert-butyl (5-oxotetrahydrofuran-3-yl)acetate

Temperature

-78 °C

Tetrahydrofuran (50 mL) and Lithium diisopropylamide mono tetrahydrofuran complex (20 mL of 1.5 M in cyclohexane) was cooled in a dry ice/Isopropanol bath for 10 min. Tert-butyl acetate (3.5 mL 26 mmoles) was added via syringe and stirred at −78° C. for 30 min. 2(5H)-Furanone (1.59 g, 19 mmoles) was added dropwise and the reaction was stirred for 1 h at −78° C. The reaction was poured into water and extracted with ether 2×150 mL The ether extracts were combined and washed with water 100 mL then brine 3×100 mL, dried and the ether removed under reduced pressure to give 2.74 g of product (72%). MS (ESI+) for C10H16O4 m/z 223 (M+Na)+.

1. stirringthe reaction was stirred for 1 h at −78° C
2. extractionextracted with ether 2×150 mL The ether extracts
3. washwashed with water 100 mL
4. dry with materialbrine 3×100 mL, dried
5. customthe ether removed under reduced pressure

ORD record

ord-46d7d26c0f8a4b6b8115e6491ccf613e

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119098B2