Reaction #672746

Reaction equation

2(5H)-Furanone

Tetrahydrofuran

Lithium diisopropylamide mono tetrahydrofuran

Tert-butyl acetate

→

product

Yield 72.0%

tert-butyl(5-oxotetrahydrofuran-3-yl)acetate

Yield 72.0%

Solvents

water

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction was stirred for 1 h at −78° C
2. 2
   Extractionextracted with ether 2×150 mL The ether extracts
3. 3
   Washwashed with water 100 mL
4. 4
   Dryingbrine 3×100 mL, dried
5. 5
   Otherthe ether removed under reduced pressure

Procedure

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)+.

Source