Reaction #165927

Reaction equation

Ethyl-2-(4,5-dihydrofuran-3-yl)-2-oxoacetate

tetrahydrofuran

N-bromosuccinimide

→

ethyl-2-(3-bromo-2-methoxytetrahydrofuran-3-yl)-2-oxoacetate

Solvents

Methanol

Conditions

Workup

1. 1
   Temperatureby maintaining temp below 0° C
2. 2
   OtherReaction mass
3. 3
   OtherReaction mass
4. 4
   Concentrationwas concentrated to residue under vacuum at 40° C
5. 5
   workup.DISSOLUTIONResidue was dissolved in Ethyl acetate (450 ml)
6. 6
   Washwashed with sodium sulphite solution (10%, 2×135 ml)
7. 7
   OtherReaction mass
8. 8
   Concentrationwas then concentrated to residue

Procedure

Ethyl-2-(4,5-dihydrofuran-3-yl)-2-oxoacetate (45 g) was dissolved in tetrahydrofuran (225 ml) and Methanol (45 ml). The reaction mass was cooled to −5 to 0° C. N-bromosuccinimide (47 g) was added lot wise by maintaining temp below 0° C. Reaction mass was then stirred at 20-25° C. for 12 hrs. Reaction mass was concentrated to residue under vacuum at 40° C. Residue was dissolved in Ethyl acetate (450 ml) and washed with sodium sulphite solution (10%, 2×135 ml). Reaction mass was then concentrated to residue to get ethyl-2-(3-bromo-2-methoxytetrahydrofuran-3-yl)-2-oxoacetate (Yield 63 g).

Source