Methyl Acrylate → 4-Cyano-4-(4-methoxy-dibenzofuran-1-yl)-heptane dioic acid dimethyl ester

HRID 2383974

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:7]=2[C:6]([CH2:16][C:17]#[N:18])=[CH:5][CH:4]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21]>C(#N)C.C(OCC)(=O)C>[CH3:24][O:23][C:19](=[O:22])[CH2:20][CH2:21][C:16]([C:17]#[N:18])([C:6]1[C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:21][CH2:20][C:19]([O:23][CH3:24])=[O:22]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (4-methoxy-dibenzofuran-1-yl)-acetonitrile (7 g, 0.029 mol) in acetonitrile (200 ml), Triton B (2.7 ml, 0.0147 mol) was added under N2 at RT. The reaction mass was heated to reflux and at reflux temperature methyl acrylate (28.25 ml, 0.295 mol) was added drop wise. The reaction mass was stirred for 4 hrs at 90° C. Once the product is formed, the reaction mass was diluted with ethyl acetate and concentrated under vacuum. 4-cyano-4-(4-methoxy-dibenzofuran-1-yl)-heptane dioic acid dimethyl ester was isolated by column chromatography. Yield 8 g (65%)

Workup

temperatureThe reaction mass was heated
temperatureto reflux
additionwas added drop wise
customOnce the product is formed
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-3f01271ada97438894fb4a32eda6e978
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263648B2

Linked notes

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