Reaction #75599

Reaction equation

(2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol

toluenesulfonyl chloride

water

→

(5R)-5-[(trityloxy)methyl]-2,2-divinyltetrahydrofuran

Yield 47.3%

Solvents

pyridine

Conditions

Workup

1. 1
   workup.STIRRINGit was stirred at room temperature for 10 min
2. 2
   ExtractionAfter extracting twice with ethyl acetate
3. 3
   Washwashed with brine
4. 4
   Dryingdried over magnesium sulfate
5. 5
   OtherThe solvent was removed
6. 6
   workup.DISSOLUTIONthe resulting residue was dissolved in toluene
7. 7
   OtherAfter the solvent was removed again
8. 8
   Otherthe resulting residue was purified by silica gel column chromatography

Procedure

13.0 g of (2S)-1-(trityloxy)-5-vinyl-6-heptene-2,5-diol and 57.2 g of toluenesulfonyl chloride were dissolved in 200 ml pyridine, and stirred at 80° C. overnight. After the reaction was completed, water was added thereto, and it was stirred at room temperature for 10 min. After extracting twice with ethyl acetate, washed with brine, and dried over magnesium sulfate. The solvent was removed, and the resulting residue was dissolved in toluene. After the solvent was removed again, the resulting residue was purified by silica gel column chromatography to give 5.88 g of (5R)-5-[(trityloxy)methyl]-2,2-divinyltetrahydrofuran.

Source