反应详情

17.13 ml (0.121 mol) of trimethylsilylacetylene and 100 ml of THF were introduced into a three-necked flask. A solution of 48.5 ml (0.121 mol) of n-butyllithium (2.5M in hexane) was added dropwise at -78° C. under a stream of nitrogen and the mixture was permitted to heat to room temperature. This solution was introduced dropwise into a solution of 23.8 g (0.11 mol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenecarboxaldehyde in 100 ml of THF at -78° C. The reaction mixture was permitted to heat to room temperature, was poured into an aqueous ammonium chloride solution and was extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of dichloromethane and hexane (50/50). After evaporating the solvents, 29.9 g (86%) of the expected alcohol were recovered in the form of a yellow oil.

1. temperatureto heat to room temperature
2. extractionwas extracted with ethyl ether
3. customThe organic phase was separated
4. dry with materialdried over magnesium sulfate
5. customevaporated
6. customThe residue obtained
7. customwas purified by chromatography on a silica column
8. washeluted with a mixture of dichloromethane and hexane (50/50)
9. customAfter evaporating the solvents, 29.9 g (86%) of the expected alcohol
10. customwere recovered in the form of a yellow oil