반응 #352489

반응 방정식

sodium hydride

2-[2-[1,3-dioxolan-2-yl]ethylthio]ethanol

mercaptoethanol

2-[2-bromoethyl]-1,3-dioxolane

triphenylphosphine

carbon tetrabromide

→

subtitled compound

2-[2-[2-Bromoethylthio]ethyl]-1,3-dioxolane

용매

acetonitrile

반응 조건

후처리

1. 1
   기타The solvent was removed under reduced pressure
2. 2
   기타the residue pre-absorbed onto silica
3. 3
   기타chromatographed over silica using 10% ethylacetate/petroleum ether as eluant

실험 절차

To a stirred cooled (<0°) solution of 2-[2-[1,3-dioxolan-2-yl]ethylthio]ethanol (13.6 g, prepared by the condensation between mercaptoethanol and 2-[2-bromoethyl]-1,3-dioxolane employing sodium hydride) in dry acetonitrile (150 ml) was added triphenylphosphine (20 g) and carbon tetrabromide (38 g). The solution was stirred for 4 hours. The solvent was removed under reduced pressure and the residue pre-absorbed onto silica. The material was flash chromatographed over silica using 10% ethylacetate/petroleum ether as eluant to afford the subtitled compound as a clear oil (4.45 g). The material was used in the next step without further purification.

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