반응 #1519085

반응 방정식

Triethylamine

ethyl 6-hydroxyhexanoate

methanesulfonyl chloride

→

compound 2

수율 85.3%

Ethyl 6-methylsulfonyloxyhexanoate

수율 85.3%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   여과The mixture was filtered through silica gel
2. 2
   세척the filtrate was washed successively with water, saturated NaHCO3, water and brine
3. 3
   건조The organics were dried over Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo to a pale yellow oil
6. 6
   기타Final purification of the crude product

실험 절차

A solution of monodispersed ethyl 6-hydroxyhexanoate (50.76 ml, 50.41 g, 227 mmol) in dry dichloromethane (75 ml) was chilled in an 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 monodispersed compound 2 (46.13 g, 85%) as a clear, colorless oil. FAB MS: m/e 239 (M+H), 193 (M-C2H5O).

출처