Reaction #85044

Reaction equation

ammonium chloride

tert-butyl 1,3-dithiane-2-carboxylate

1-iodo-2-methoxyethane

potassium tert-butoxide

→

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

Solvents

dimethylformamide

Conditions

Workup

1. 1
   OtherThe resulting reaction mixture
2. 2
   Extractionextracted three times with 300 ml of diethyl ether
3. 3
   DryingThe combined organic phases were dried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Otherthe solvent was removed under reduced pressure
6. 6
   OtherThe crude product was used for the next step without further purification

Procedure

10.2 g (46.1 mmol) of tert-butyl 1,3-dithiane-2-carboxylate and 12.0 g (64.5 mmol) of 1-iodo-2-methoxyethane were initially charged in 127 ml of dimethylformamide, the mixture was cooled to 0° C. and 6.21 g (55.3 mmol) of potassium tert-butoxide were added. The resulting reaction mixture was stirred at 0° C. for 1 h and at RT for 16 h. The reaction mixture was added to 1.5 l of a 1:2 mixture of ice and saturated aqueous ammonium chloride solution and extracted three times with 300 ml of diethyl ether. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product was used for the next step without further purification. Yield: 11.1 g (87% of theory)

Source