반응 #50481

반응 방정식

(E)-3,7-dimethyl-2,6-octadien-1-ol

2,4,6-collidine

lithium chloride

→

pale yellow oil

수율 89.4%

(E)-8-Chloro-2,6-dimethyl-2,6-octadiene

수율 89.4%

용매

DMF

반응 조건

후처리

1. 1
   세척The aqueous solution was washed three times with 200 mL portions of hexane
2. 2
   세척washed with 5% KHSO4, water, NaHCO3, brine
3. 3
   건조dried (MgSO4)
4. 4
   기타evaporated

실험 절차

To a stirred solution of 30.0 g (0.194 mol) of (E)-3,7-dimethyl-2,6-octadien-1-ol and 28.27 mL (0.213 mol) of 2,4,6-collidine under argon at room temperature was added dropwise 8.23 g (0.194 mol) of lithium chloride in 100 mL of DMF. The mixture was cooled to 0° C. and treated with 16.56 mL (0.213 mmol) of methanesulfonyl chloride dropwise over 10 minutes. The reaction was stirred at 0° C. for 1.5 hours (solid present), then was poured into 500 mL of ice/water. The aqueous solution was washed three times with 200 mL portions of hexane, the organic layers were combined and washed with 5% KHSO4, water, NaHCO3, brine, dried (MgSO4) and evaporated to provide 29.95 g of a pale yellow oil. Rapid flash chromatography was performed on 400 g of silica gel, eluting with 3:9 EtOAc/hexane. Pure product fractions were combined and evaporated to provide 25.20 g (75%) of title compound as a pale yellow oil.

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