Reaktion #76836

Reaktionsgleichung

tosyl chloride

crude product

(2R)-2-acetoxymethyl-4,4-diethoxy-butanol

CH2Cl2

Et3N

→

(2S)-2-acetoxymethyl-4,4-diethoxybutyl toluenesulfonate

Lösungsmittel

H2O

EtOAc

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 100 mL 1-neck round bottom flask, equipped with a magnetic stir bar
2. 2
   Sonstigethe aqueous layer was separated
3. 3
   workup.ADDITIONTo the organic layer was added 75 ml of a 5% aq. solution of KH2PO4
4. 4
   workup.ADDITIONAfter mixing
5. 5
   Sonstigeseparation of the layers
6. 6
   Sonstigethe aqueous layer was removed
7. 7
   WaschenThe organic layer was washed with 50 mL of saturated NaHCO3 solution
8. 8
   Trocknendried over Na2SO4
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated in vacuo to a constant weight of 7.40 g of the desired product

Vorschrift

Into a 100 mL 1-neck round bottom flask, equipped with a magnetic stir bar and septum under N2 was charged the crude product of Example 14 step c) (4.62 g, 19 mmol), dry CH2Cl2 (20 mL) and Et3N (5.62 mL, 40 mmol). To this solution was added tosyl chloride (4.76 g, 25 mmol). The resulting mixture was stirred at ambient temperature for 4 hours. Charged H2O (0.27 g, 15 mmol) and stirred vigorously for 4 hours. The reaction mixture was diluted with 80 mL EtOAc and 50 mL H2O and the aqueous layer was separated. To the organic layer was added 75 ml of a 5% aq. solution of KH2PO4. After mixing and separation of the layers, the aqueous layer was removed. The organic layer was washed with 50 mL of saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated in vacuo to a constant weight of 7.40 g of the desired product.

Quelle