Reaktion #81756

Reaktionsgleichung

HCl

methanesulfonyl chloride

2-decanol

diisopropylethylamine

→

2-methanesulfonyloxydecane

Ausbeute 105.8%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction flask was immersed in an ice/water bath
2. 2
   workup.STIRRINGAfter stirring for 3 hrs
3. 3
   SonstigeThe layers were separated
4. 4
   Waschenthe organic phase washed with cold 5% aqueous HCl (50 ml)
5. 5
   TrocknenThe CH2Cl2 layer was dried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated in vacuo at 25° C
8. 8
   workup.WAITThe resulting light yellow oil was pumped under reduced pressure for 2 hrs

Vorschrift

To a solution of 2-decanol (5.0 ml, 26.0 mmol) in dry CH2Cl2 (52 ml) under an N2 atmosphere was added diisopropylethylamine (5.6 ml, 32.1 mmol). The reaction flask was immersed in an ice/water bath. After stirring for 10 minutes, methanesulfonyl chloride (2.8 ml, 36.1 mmol) was added via syringe over a period of 10 minutes. After stirring for 3 hrs, the reaction was diluted with cold CH2Cl2 (200 ml) and poured into cold 5% aqueous HCl (100 ml). The layers were separated and the organic phase washed with cold 5% aqueous HCl (50 ml) followed by brine (2×50 ml). The CH2Cl2 layer was dried (Na2SO4), filtered and evaporated in vacuo at 25° C. The resulting light yellow oil was pumped under reduced pressure for 2 hrs to provide 2-methanesulfonyloxydecane (6.5 g, 93.5%) as a light yellow oil.

Quelle