Hydrochloric Acid → 7-Octen-1-ol, 7-methyl-3-methylene-

2.1 Grams (10.0 mmol) of the above complex is suspended in 15 ml of dry ether, and 12 ml of dimethyl sulfide is added under nitrogen. The resulting solution is cooled to -60° and another 14 ml of dimethyl suflide is added to dissolve the precipitate that forms. The Grignard reagent (24 ml, 9.6 mmol) from B above is added at -60° over 5 min and the reaction is stirred at -45° for 2 hr. Trimethylsilyl 3-butynyl ether (1.4 g, 9.8 mmol) (preparation follows) in ether/pentane (5 ml/30 ml) is added at -45°; the mixture is allowed to warm to -25° with stirring for several hours. The reaction is then poured into a pre-cooled (<-10°) solution of HCl/sat. NH4Cl, allowed to warn to RT and stirred overnight. The reaction is worked up by water and extraction with ether (2×). The ether phases are combined, washed with sat (NH4)2SO4, water and brine, filtered and solvent removed to give 7-methyl-3-methylene-7-octen-1ol.

1. temperatureThe resulting solution is cooled to -60°
2. additionanother 14 ml of dimethyl suflide is added
3. dissolutionto dissolve the precipitate that forms
4. temperatureto warm to -25°
5. stirringwith stirring for several hours
6. additionThe reaction is then poured into
7. customto warn to RT
8. stirringstirred overnight
9. extractionThe reaction is worked up by water and extraction with ether (2×)
10. washwashed with sat (NH4)2SO4, water and brine
11. filtrationfiltered
12. customsolvent removed

ORD record

ord-f90f07a66ccb40a5a4e12733cb896cd1

Source dataset

uspto-grants-1981_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04264518