Metaperiodic acid → 6-(Ethoxycarbonyl)-4-(4-(methylsulfonyl)phenoxy)benzofuran-2-carboxylic acid

HRID 1643752Notes

Reaction equation

HRID 1643752 reaction equation
I(O)(=O)(=O)=[O:2].[CH:6]([C:8]1[O:9][C:10]2[CH:16]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:14]=[C:13]([O:22][C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[C:11]=2[CH:12]=1)=[O:7]>CC#N.C(OCC)(=O)C.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](F)([O-])(=O)=O>[CH2:20]([O:19][C:17]([C:15]1[CH:14]=[C:13]([O:22][C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)[C:11]2[CH:12]=[C:8]([C:6]([OH:2])=[O:7])[O:9][C:10]=2[CH:16]=1)=[O:18])[CH3:21]

Participants

6

Reactant 2

HCID 65185Metaperiodic acidHCID 86624767Ethyl 2-formyl-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate

Product 1

HCID 667562256-(Ethoxycarbonyl)-4-(4-(methylsulfonyl)phenoxy)benzofuran-2-carboxylic acidYield 95%

Reagents, catalysts & solvents 3

HCID 178479089HCID 178479089, compoundCatalystHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 10 mL of acetonitrile was added periodic acid (232 mg, 1.02 mmol), and the solution was stirred vigorously at room temperature for 15 min. Ethyl 2-formyl-4-(4-(methylsulfonyl)phenoxy)-benzofuran-6-carboxylate (360 mg, 0.927 mmol) was then added at 0° C. followed by the addition of pyridium fluorochromate (3.69 mg, 0.0185 mmol) in CH3CN (1 mL). The reaction was stirred at 0° C. for 1 hour. The reaction was diluted with ethyl acetate and washed with brine. The organic layer was dried and concentrated to give the title compound (355 mg, 95%) as an orange solid. The crude product was used in the next step without further purification. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.40 (t, J=7.16 Hz, 3 H) 3.09 (s, 3 H) 4.41 (q, J=7.16 Hz, 2 H) 7.12-7.22 (m, 2 H) 7.55 (d, J=1.13 Hz, 1 H) 7.63 (d, J=1.13 Hz, 1 H) 7.92-8.02 (m, 2 H) 8.17 (s, 1 H).

Workup

  1. stirringThe reaction was stirred at 0° C. for 1 hour
  2. washwashed with brine
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5a9c5757ac354ff8b574462f03420557
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…