Dimethyl Sulfoxide → 4-Chloroheptane-3,5-dione

Chlorotrimethylsilane (29.7 ml, 0.234 mol) was added dropwise to a stirred pale yellow solution of tetrabutylammonium bromide (1.26 g, 3.9 mmol) in dry acetonitrile (116 ml) at room temperature under nitrogen. The resulting solution was cooled in ice and 3,5-heptanedione (10.6 ml, 78.0 mmol) and then dry dimethylsulphoxide (16.6 ml, 0.234 mol) were added dropwise over 5 minutes producing a yellow solution which was allowed to warm slowly to room temperature, with stirring, over 4 hours. The mixture was diluted with water (1 liter), stirred for 10 min and then extracted with ether (1×500 ml, 2×250 ml). The combined ether layers were dried over magnesium sulphate, filtered and concentrated under reduced pressure to leave a yellow oil. The crude product was purified by distillation under reduced pressure to afford the title compound (5.5 g) as a pale yellow oil, b.p. 102–105° C./54 mmHg containing ca. 10% 4,4-dichloro-3,5-heptanedione as estimated by microanalysis.

1. temperatureThe resulting solution was cooled in ice
2. customproducing a yellow solution which
3. stirringstirred for 10 min
4. extractionextracted with ether (1×500 ml, 2×250 ml)
5. dry with materialThe combined ether layers were dried over magnesium sulphate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto leave a yellow oil
9. distillationThe crude product was purified by distillation under reduced pressure

ORD record

ord-2de9074eff724f52831c883ffe26589a

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07141585B2