Ethanol → Ethyl-2-(2-ethoxytetrahydrofuran-3-yl)-2-oxoacetate

Temperature

7.5 °C

Ethyl-2-(4,5-dihydrofuran-3-yl)-2-oxoacetate (100 g) was dissolved in dichloromethane (500 ml). Ethanol (150 ml) was added to reaction mass and then reaction mass was cooled to 5 to 10° C. N-bromosuccinimide (115 g) was added lot wise by maintaining temp below 10° C. Reaction mass was then stirred at 20-30° C. till completion of reaction. Reaction mass was washed with sodium bicarbonate solution (8%, 3×400 ml). Sodium sulphite solution (15%, 1700 ml) was charged to dichloromethane layer. Reaction mass was stirred for 8 hrs at 25-35° C. Organic and aqueous layer separated. Dichloromethane layer was washed with water (2×340 ml). Dichloromethane layer was then concentrated to residue to get Ethyl-2-(2-ethoxytetrahydrofuran-3-yl)-2-oxoacetate (Yield 114 g)

1. customreaction mass
2. temperatureby maintaining temp below 10° C
3. customReaction mass
4. customReaction mass
5. washwas washed with sodium bicarbonate solution (8%, 3×400 ml)
6. additionSodium sulphite solution (15%, 1700 ml) was charged to dichloromethane layer
7. customReaction mass
8. stirringwas stirred for 8 hrs at 25-35° C
9. customOrganic and aqueous layer separated
10. washDichloromethane layer was washed with water (2×340 ml)
11. concentrationDichloromethane layer was then concentrated to residue

ORD record

ord-95f55e150f2a4274979fca4084e900ca

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841467B2