[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6]O)[CH2:2]1.O1CCC(C=O)C1.O1CCCC1C[CH2:21][CH2:22][NH2:23].[Cl-].C(C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#N>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.CCOCC.C(Cl)Cl>[O:1]1[CH2:5][CH2:4][CH:3]([CH:6]=[CH:21][C:22]#[N:23])[CH2:2]1Tetrahydro-3-furanmethanol (0.96 mL, 10 mmol) was oxidized to tetrahydrofuran-3-carbaldehyde (assume 50%) via the TPAP/MNO oxidation procedure described for 3-(tetrahydro-furan-2-yl)-propylamine. Wittig reaction of the crude aldehyde with (cyanomethyl)triphenylphosphonium chloride as described for 3-(tetrahydrofuran-2-yl)propylaamine gave 3-(tetrahydrofuran-3-yl)acrylonitrile (3.3 mmol) as a 2:1 mixture (1H NMR) of the E/Z isomers after column chromatography (10% Et2O/CH2Cl2 elutant). Hydrogenation of 3-(tetrahydrofuran-3-yl)acrylonitrile in the presence of Raney Ni as detailed for 3-(tetrahydro-furan-2-yl)-propylamine gave 3-(tetrahydrofuran-3-yl) propylamine. (33% yield). ESI-MS (m/z) 130 [M+H]+.
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