Reaktion #353419

Reaktionsgleichung

1,5-pentanediol

triethylamine

methanesulfonylchloride

→

5-hydroxypentylmethylsulfonate

Ausbeute 56.5%

Lösungsmittel

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat -4° C. for 18 hours
2. 2
   WaschenThe reaction mixture was washed with H2O, 1N HCl, H2O
3. 3
   Sonstigedried
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residual oil was chromatographed on a silica gel column
6. 6
   Wascheneluting with EtOAc-CH2Cl2 (2:8)

Vorschrift

To a solution of 85.0 g (0.904 mole) of 1,5-pentanediol and 30.3 g (0.30 mole) of triethylamine in 350 mL of dry CH2Cl2 at -20° C. was added dropwise a solution of 28.5 g (0.25 mole) of methanesulfonylchloride in 100 mL of CH2Cl2 over 2 hours under nitrogen atmosphere. The solution was stirred at 2 hours at -20° C. and then at -4° C. for 18 hours. The reaction mixture was washed with H2O, 1N HCl, H2O, then dried and evaporated. The residual oil was chromatographed on a silica gel column, eluting with EtOAc-CH2Cl2 (2:8). After combining the appropriate fractions there was obtained 25.7 g (56.5%) of 5-hydroxypentylmethylsulfonate as a colorless oil.

Quelle