1-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acid → 1-(Benzofuran-5-yl)cyclopropanecarboxylic acid

HRID 468250

Reaction equation

C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)C>C1(C)C(C)=CC=CC=1>[O:6]1[C:7]2[CH:12]=[CH:11][C:10]([C:13]3([C:16]([OH:18])=[O:17])[CH2:15][CH2:14]3)=[CH:9][C:8]=2[CH:4]=[CH:5]1

Participants

Conditions

Temperature: 140 °C

Procedure

To a suspension of 1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid (20 g, ˜65 mmol) in xylene (100 mL) was added PPA (22.2 g, 64.9 mmol) at room temperature. The mixture was heated at reflux (140° C.) for 1 hour before it was cooled to room temperature and decanted from the PPA. The solvent was evaporated under vacuum to obtain the crude product, which was purified by preparative HPLC to provide 1-(benzofuran-5-yl)cyclopropanecarboxylic acid (1.5 g, 5%). 1H NMR (400 MHz, DMSO-d6) δ 12.25 (br s, 1H), 7.95 (d, J=2.8 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.47 (d, J=11.6 Hz, 1H), 7.25 (dd, J=2.4, 11.2 Hz, 1H), 6.89 (d, J=1.6 Hz, 1H), 1.47-1.44 (m, 2H), 1.17-1.14 (m, 2H).

Workup

additionwas added PPA (22.2 g, 64.9 mmol) at room temperature
temperatureThe mixture was heated
temperaturewas cooled to room temperature
customdecanted from the PPA
customThe solvent was evaporated under vacuum
customto obtain the crude product, which
customwas purified by preparative HPLC

Sources & evidence

ORD record: ord-f707005eb6de41b6a29f8709d6bb7dae
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623905B2

Linked notes

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