Reaktion #6728

Reaktionsgleichung

Triethylamine

ethyl 6-hydroxyhexanoate

methanesulfonyl chloride

→

product

Ausbeute 85.3%

Ethyl 6-methylsulfonyloxyhexanoate

Ausbeute 85.3%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered through silica gel
2. 2
   Waschenthe filtrate was washed successively with water, saturated NaHCO3, water and brine
3. 3
   TrocknenThe organics were dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo to a pale yellow oil
6. 6
   SonstigeFinal purification of the crude product

Vorschrift

A solution of non-polydispersed ethyl 6-hydroxyhexanoate (50.76 ml, 50.41 g, 227 mmol) in dry dichloromethane (75 ml) was chilled in a ice bath and placed under a nitrogen atmosphere. Triethylamine (34.43 ml, 24.99 g, 247 mmol) was added. A solution of methanesulfonyl chloride (19.15 ml, 28.3 g, 247 mmol) in dry dichloromethane (75 ml) was added dropwise from an addition funnel. The mixture was stirred for three and one half hours, slowly being allowed to come to room temperature as the ice bath melted. The mixture was filtered through silica gel, and the filtrate was washed successively with water, saturated NaHCO3, water and brine. The organics were dried over Na2SO4, filtered and concentrated in vacuo to a pale yellow oil. Final purification of the crude product was achieved by flash chromatography (silica gel, 1/1 hexanes/ethyl acetate) to give the non-polydispersed product (46.13 g, 85%) as a clear, colorless oil. FAB MS: m/e 239 (M+H), 193 (M-C2H5O).

Quelle