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

HRID 1822808Notes

Reaction equation

HRID 1822808 reaction equation
[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]1

Participants

7

Reactant 4

HCID 139980Tetrahydro-3-furanmethanolHCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 197040(Cyanomethyl)triphenylphosphonium chlorideHCID 221700413-(Tetrahydrofuran-2-yl)propan-1-amine

Product 1

HCID 695277853-(Tetrahydrofuran-3-yl)acrylonitrile

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

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]+.

Sources & evidence

ORD record
ord-a40ea51a78ac4c139154d384a5ed9a85
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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