Tetrahydro-3-furanmethanol → 3-(Tetrahydrofuran-3-yl)acrylonitrile

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Reaction Steps

Tetrahydro-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]+.

Provenance & Evidence