Tetrahydrofuran → 5-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

HRID 2396018Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:13])[CH2:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([N-]C(C)C)(C)C.[Li+].O1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:1][O:2][C:3](=[O:13])[CH:4]([CH2:26][CH2:25][CH:24]=[CH2:23])[N:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724682Lithium diisopropylamide

HCID 4169153Methyl [(phenylmethylidene)amino]acetate

Product 1

HCID 120394615-Hexenoic acid, 2-[(phenylmethylene)amino]-, methyl ester

Procedure

In step a, the N-(phenylmethylene)glycine methyl ester of structure 55 can be treated with one equivalent of a non-nucleophilic base, such as lithiumdiisopropylamide, in a suitable aprotic solvent, such as tetrahydrofuran, followed by addition of a 4-halobutene of structure 56 to give 2-(3-butenyl)-N-(phenylmethylene)glycine methyl ester of structure 57.

Sources & evidence

ORD record: ord-bcbc13e6d5b746c9a1bb3a9632be3e4c
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491143

Reaction notes

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