C[Si](C)(C)C#C[CH:5]1[CH2:14][C:13]([CH3:16])([CH3:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:17][OH:18])[CH:11]=2)[S:6]1.[CH2:21]1COC[CH2:22]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:21]([CH:17]([C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[S:6][CH2:5][CH2:14][C:13]2([CH3:15])[CH3:16])[OH:18])#[CH:22]5.9 g (19.4 mmol) of α-trimethylsilylethynyl-4,4-dimethyl-6-thiochromanmethanol and 50 ml of THF were introduced into a round-bottomed flask and 21.3 ml (23.3 mmol) of a tetrabutylammonium fluoride solution (1.1M in THF) were added dropwise. Stirring was carried out at room temperature for 1 hour and the reaction mixture was poured into water and 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 ethyl acetate and hexane (1/4). After evaporating the solvents, 3.9 g (87%) of α-ethynyl-4,4-dimethyl-6-thiochromanmethanol were recovered in the form of a colorless oil.
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