[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([CH3:31])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:20]3[CH:30]=[CH:29][C:23]([C:24](OCC)=[O:25])=[CH:22][N:21]=3)[CH:16]=2)[S:11][CH2:10][CH2:9]1.O>C1COCC1>[CH3:7][C:8]1([CH3:31])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]#[C:19][C:20]3[N:21]=[CH:22][C:23]([CH2:24][OH:25])=[CH:29][CH:30]=3)[CH:16]=2)[S:11][CH2:10][CH2:9]1To 3.0 ml of 1M lithium aluminum hydride (3.0 mmol) in THF, cooled to -78° C., was added dropwise over 5 min a solution of 2.0 g (5.9 mmol) of ethyl 6-(2-(4,4-dimethylthiochroman-6-yl)-ethynyl)nicotinate in 5 ml of THF. The reaction mixture was stirred at -78° C. for 40 min and then treated with 2 ml of water. The mixture was warmed to room temperature and the organic layer was separated. The aqueous layer was extracted with 3×10 ml of ether. The organic extracts were combined and washed successively with 1×10 ml of dilute HCl, 3×10 ml of water and 1×15 ml of saturated NaCl solution and then dried (MgSO4). The solvent was removed in vacuo and the residue purified by flash chromatography (silica; 50% ethyl acetate in hexanes) to give the title compound as a pale yellow solid.
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