[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:10]1[CH:14]=[C:13]([C:15](OCC)=[O:16])[C:12]([C:20]([F:23])([F:22])[F:21])=[CH:11]1)[C:8]#[CH:9].[H-].[K].[Na]>O1CCCC1.C(OCC)(=O)C>[CH2:7]([N:10]1[CH:14]=[C:13]([CH2:15][OH:16])[C:12]([C:20]([F:23])([F:21])[F:22])=[CH:11]1)[C:8]#[CH:9]At 0° C., 1.95 g of lithium aluminium hydride were introduced in small portions into a solution of 12.6 g of ethyl 1-(2-propynyl)-3-trifluoromethyl-1H-pyrrole-4-carboxylate in 65 ml of tetrahydrofuran with stirring for 2 hours at 20° C. 10 ml of ethyl acetate were added to eliminate possible excess of hydride and the reaction mixture was poured into a saturated solution of sodium-potassium double tartrate. After extraction with ethyl acetate, the extracts were concentrated to dryness by distillation under reduced pressure. The residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (7-3) to obtain 5.7 g of 1-(2-propynyl)-3-trifluoromethyl-1H-pyrrole-4-methanol melting at 45° C.
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