Malonic Acid → (2E)-3-(1-Benzofuran-2-yl)acrylic acid

HRID 2178717Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15].N1CCCCC1>>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1/[CH:10]=[CH:13]/[C:14]([OH:16])=[O:15]

Participants

Reactant 3

HCID 867Malonic Acid

HCID 8082Piperidine

HCID 613412-Benzofurancarboxaldehyde

Product 1

HCID 12589383(2E)-3-(1-Benzofuran-2-yl)acrylic acid

Procedure

A mixture of 1-benzofuran-2-carbaldehyde and propanedioic acid was treated with piperidine to give (2E)-3-(1-benzofuran-2-yl)prop-2-enoic acid. The resulting acid was converted to the acyl azide, then cyclized to [1]benzofuro[3,2-c]pyridin-1(2H)-one with tri-n-butylamine at 180° C. Treatment with phosphorus oxychloride provided 1-chloro[1]benzofuro[3,2-c]pyridine, which was converted to the requisite 2-aminoethanol according to the method of footnote 32.

Sources & evidence

ORD record: ord-c040dcd5ae4549139d1706228fa723bb
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067934B2

Reaction notes

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