Iodine → 6,6-Dimethyl-1-heptene

A solution of 2,2-Dimethylpropane (15.1 g, 0.10 mol) in dry tetrahydrofuran (80 ml) was added dropwise to a mixture of magnesium turnings (2.43 g, 0.10 mol) in dry tetrahydrofuran (20 ml) containing a single crystal of iodine, at such a rate so as to maintain the solvent at reflux. The resulting solution was allowed to cool to room temperature and decanted from the residual magnesium under nitrogen into a fresh flask. The solution was diluted with dry tetrahydrofuran (150 ml), cooled to -20° C. under an atmosphere of nitrogen treated with cuprous bromide dimethyl sulphide complex and stirred for 20 minutes. The resulting solution was then treated with 4-bromo-1-butene (13.5 g, 0.10 mol) and stirred at -20° C. for 16 hours and then at 20° C. for 4 hours. The reaction mixture as quenched with saturated aqueous ammonium chloride solution (10 ml), diluted with ether (200 ml) and washed with an aqueous solution of ammonia (2×200 ml of 10%). The solution was dried over sodium sulfate and distilled at atmospheric pressure to yield 6,6-dimethyl- 1-heptene as a colourless oil, having a boiling point of 120°-125° C., and the following structural characteristics:

1. temperatureat such a rate so as to maintain the solvent
2. temperatureat reflux
3. customdecanted from the residual magnesium under nitrogen into a fresh flask
4. additionThe solution was diluted with dry tetrahydrofuran (150 ml)
5. temperaturecooled to -20° C. under an atmosphere of nitrogen
6. additiontreated with cuprous bromide dimethyl sulphide complex
7. stirringstirred at -20° C. for 16 hours
8. waitat 20° C. for 4 hours
9. customThe reaction mixture as quenched with saturated aqueous ammonium chloride solution (10 ml)
10. additiondiluted with ether (200 ml)
11. washwashed with an aqueous solution of ammonia (2×200 ml of 10%)
12. dry with materialThe solution was dried over sodium sulfate
13. distillationdistilled at atmospheric pressure

ORDレコード

ord-bfdb595376384f2ba24e31c6ab9ed302

出典データセット

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04837333