HCID 59129204, compound → HCID 59129301, compound

HRID 1991616Notes

Reaction equation

HRID 1991616 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1>CO.O=[Pt]=O>[O:1]1[C:5]2[CH:6]=[C:7]([C:10]3([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]3)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 59129204HCID 59129204, compound

Product 1

HCID 59129301HCID 59129301, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-(benzofuran-6-yl)cyclopropanecarboxylic acid (370 mg, 1.8 mmol) in MeOH (50 mL) was added PtO2 (75 mg, 20%) at room temperature. The reaction mixture was stirred under hydrogen atmosphere (1 atm) at 20° C. for 3 d. The reaction mixture was filtered and the solvent was evaporated in vacuo to afford the crude product, which was purified by prepared HPLC to give 1-(2,3-dihydrobenzofuran-6-yl)cyclopropanecarboxylic acid (155 mg, 42%). 1H NMR (300 MHz, MeOD) δ 7.13 (d, J=7.5 Hz, 1H), 6.83 (d, J=7.8 Hz, 1H), 6.74 (s, 1H), 4.55 (t, J=8.7 Hz, 2H), 3.18 (t, J=8.7 Hz, 2H), 1.56-1.53 (m, 2H), 1.19-1.15 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated in vacuo
  3. customto afford the crude product, which
  4. customwas purified
  5. customby prepared HPLC

Sources & evidence

ORD record
ord-c81e34d224224933a6812d2926db34e2
Source dataset
uspto-grants-2010_01
Patent number
US07645789B2

Reaction notes

Loading…