[CH2:1]([N:4]1[CH:8]=[C:7]([CH:9]=[O:10])[CH:6]=[C:5]1[C:11]#[N:12])[CH:2]=[CH2:3].[C:13]([Si](C)(C)C)([F:16])([F:15])[F:14].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([N:4]1[CH:8]=[C:7]([CH:9]([OH:10])[C:13]([F:16])([F:15])[F:14])[CH:6]=[C:5]1[C:11]#[N:12])[CH:2]=[CH2:3]To a chilled (0° C.) solution of 1-allyl-4-formyl-1H-pyrrole-2-carbonitrile (1.25 g, 7.8 mmol, 1 equiv.) in 10 mL of THF was added CF3TMS (1.5 ml, 9.5 mmol, 1.2 equiv.) dropwise followed by TBAF (1M in THF, 9.4 ml, 9.4 mmol, 1.2 equiv.) slowly dropwise. The cold bath was then removed and the mixture was stirred at room temperature. After 2 hours, the reaction was quenched with water and extracted with EtOAc. The organic was dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography eluting with EtOAc-hexanes (5-40% gradient) to afford 1-allyl-4-(2,2,2-trifluoro-1-hydroxyethyl)-1H-pyrrole-2-carbonitrile which was used without further purification.
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