Reaction #85045

Reaction equation

tert-butyl 2-(2-methoxyethyl)-1,3-dithiane-2-carboxylate

N-bromosuccinimide

→

tert-Butyl 4-methoxy-2-oxobutanoate

Solvents

acetone

water

acetone

water

Conditions

Workup

1. 1
   Otherdid not exceed −5° C
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Otherthe reaction was then terminated
4. 4
   workup.ADDITION420 ml of n-heptane were added to the reaction mixture
5. 5
   Otherafter phase separation
6. 6
   Extractionthe aqueous phase was extracted three times with 315 ml of ethyl acetate
7. 7
   DryingThe combined organic phases were dried over sodium sulphate
8. 8
   Filtrationfiltered
9. 9
   Otherthe solvent was removed at 25° C.
10. 10
    workup.STIRRINGThe resulting suspension was stirred with 100 ml of n-hexane
11. 11
    Filtrationthe precipitate was filtered off
12. 12
    OtherThe solvent was removed under reduced pressure
13. 13
    Othergiving the target compound

Procedure

A solution of 10.6 g (38.1 mmol) of tert-butyl 2-(2-methoxyethyl)-1,3-dithiane-2-carboxylate in 365 ml of acetone and 18 ml of water was added dropwise to a solution, cooled to −18° C., of 54.2 g (305 mmol) of N-bromosuccinimide in 365 ml of acetone and 18 ml of water such that the internal temperature did not exceed −5° C. After the addition had ended, the mixture was stirred for another 10 min and the reaction was then terminated using 630 ml of sodium sulphite solution (1N). 420 ml of n-heptane were added to the reaction mixture and, after phase separation, the aqueous phase was extracted three times with 315 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed at 25° C. and 75 mbar. The resulting suspension was stirred with 100 ml of n-hexane and the precipitate was filtered off. The solvent was removed under reduced pressure, giving the target compound. Yield: 5.28 g (59% of theory)

Source