1-(Benzofuran-5-yl)cyclopropanecarboxylic acid → 1-(2,3-Dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid

HRID 881084Notes

Reaction equation

HRID 881084 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1>CO.O=[Pt]=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 513584541-(Benzofuran-5-yl)cyclopropanecarboxylic acid

Product 1

HCID 513584551-(2,3-Dihydrobenzofuran-5-yl)cyclopropanecarboxylic acidYield 47%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(benzofuran-5-yl)cyclopropanecarboxylic acid (700 mg, 3.47 mmol) in MeOH (10 mL) was added PtO2 (140 mg, 20%) at room temperature. The stirred reaction mixture was hydrogenated under hydrogen (1 atm) at 10° C. for 3 days. The reaction mixture was filtered. The solvent was evaporated under vacuum to afford the crude product, which was purified by preparative HPLC to give 1-(2,3-dihydrobenzofuran-5-yl)cyclopropanecarboxylic acid (330 mg, 47%). 1H NMR (400 MHz, CDCl3) δ 7.20 (s, 1 H), 7.10 (d, J=10.8 Hz, 1 H), 6.73 (d, J=11.2 Hz, 1 H), 4.57 (t, J=11.6 Hz, 2 H), 3.20 (t, J=11.6 Hz, 2 H), 1.67-1.63 (m, 2 H), 1.25-1.21 (m, 2 H).

Workup

  1. customThe stirred reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. customThe solvent was evaporated under vacuum
  4. customto afford the crude product, which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-a449826b49f34eecbd4711ca0259e555
Source dataset
uspto-grants-2015_03
Patent number
US08993600B2

Reaction notes

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