Reaction #431052

Reaction equation

2-fluoroethanol

4-hydroxy-5-chloro-6-ethoxycarbonyl-8-flurothiochroman

→

4-(2-fluoroethoxy)-5-chloro-6-ethoxycarbonyl-8-fluorothiochroman

Yield 79.0%

Conditions

Workup

1. 1
   Temperaturewas refluxed
2. 2
   Temperatureunder heat for 5 hours
3. 3
   Temperatureto cool
4. 4
   workup.ADDITIONthe reaction mixture was poured into an ice bath
5. 5
   Extractionextracted with ethyl acetate twice
6. 6
   WashAn organic layer was washed with a saturated sodium chloride aqueous solution
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off

Procedure

5 ml of 2-fluoroethanol and 3 drops of concentrated sulfuric acid were added to 2.4 g (8.2 mmol) of 4-hydroxy-5-chloro-6-ethoxycarbonyl-8-flurothiochroman (corresponding to compound of the formula (IX)), and the mixture was refluxed under heat for 5 hours. After allowed to cool, the reaction mixture was poured into an ice bath, and extracted with ethyl acetate twice. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and the solvent was distilled off to give 2.2 g (yield 79%) of 4-(2-fluoroethoxy)-5-chloro-6-ethoxycarbonyl-8-fluorothiochroman (corresponding to compound of the formula (X)).

Source