C([Cu])#N.C([Li])CCC.[SnH:9]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH2:12][CH3:13].[H][H].[CH3:24]/[C:25](/[C:29]#[CH:30])=[CH:26]\[CH2:27][OH:28].[NH4+].[OH-].[NH4+].[Cl-]>C1COCC1>[CH2:18]([Sn:9]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:14][CH2:15][CH2:16][CH3:17])/[CH:30]=[CH:29]/[C:25](/[CH3:24])=[CH:26]/[CH2:27][OH:28])[CH2:19][CH2:20][CH3:21]CuCN (2.01 g, 22.40 mmol) is introduced into a round-bottomed flask placed under argon, THF (60 ml) is then added and the mixture is cooled to −78° C. n-Butyl-lithium (1.6M, 27.7 ml, 44.40 mmol) is then added drop-wise and the mixture is allowed to slowly return to room temperature. It is again cooled to −78° C. and n-Bu3SnH (12 ml, 44.40 mmol) is added and the mixture is stirred for minutes, during which the hydrogen is discharged (2E)-3-Methylpent-2-en-4-yn-1-ol (1.86 g, 19.31 mmol) is then added, the reaction mixture is left stirring for 45 minutes and then poured into 200 ml of an NH4OH/NH4Cl (10/90) solution. Extraction is carried out with ether (3×100 ml), drying is carried out over Na2SO4 and evaporation is carried out under vacuum.
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