C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])(C)C.[F-].[K+].[BH4-].[Na+].[NH4+].[Cl-]>CO>[C:6]([C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=1)#[CH:5]To 3-trimethylsilanylethynyl-benzaldehyde 73(a1) from step 1a in methanol (540 mL, 0.3 M) was added KF (18.8 g, 324 mmol), and the resulting mixture stirred at 22° C. for 6 hours. After cooling to 0° C., NaBH4 (6.13 g, 162 mmol) was carefully added over 0.5 hours. Aqueous saturated NH4Cl was carefully added and the volatiles were removed in vacuo. Ethyl acetate (200 mL) was added, and the organic phase was washed with water and a saturated aqueous NaCl solution, dried over MgSO4 and filtered. The volatiles were removed in vacuo to afford crude (3-ethynyl-phenyl)-methanol 73(a2).
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