反应详情

Oxalyl chloride (12.7 g, 100.0 mmol) was added dropwise during 20 min to a stirred solution of (Z)-3-hexenol (20.0 g, 200.0 mmol) in pyridine (240 mL) at 0° C. The reaction mixture was allowed to warm up to room temperature during the week-end, then added to H2SO4 (50%, containing ice, 400 mL), extracted with ether (400 mL and 200 mL), treated again with H2SO4 (50%, containing ice, 400 mL), washed with a saturated solution of NaCl (200 mL) and a saturated solution of NaHCO3 (200 mL, 2×). The organic layer was dried (Na2SO4) and concentrated. Column chromatography (SiO2, heptane/diethyl ether 9:1) gave, after drying under vacuum (0.5 mbar, 1 h), 20.9 g (82%) of an oil.

1. extractionextracted with ether (400 mL and 200 mL)
2. additiontreated again with H2SO4 (50%, containing ice, 400 mL)
3. washwashed with a saturated solution of NaCl (200 mL)
4. dry with materialThe organic layer was dried (Na2SO4)
5. concentrationconcentrated
6. customColumn chromatography (SiO2, heptane/diethyl ether 9:1) gave
7. dry with materialafter drying under vacuum (0.5 mbar, 1 h), 20.9 g (82%) of an oil