Pyridinium chloride → HCID 22221622, compound

HRID 1836038Notes

Reaction equation

HRID 1836038 reaction equation
[CH:1]([C:4]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:9][C:8]=2[CH:7]=[C:6]([O:21]C)[CH:5]=1)([CH3:3])[CH3:2].Cl.N1C=CC=CC=1>O>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]2[O:11][C:12]3[C:4]([CH:1]([CH3:2])[CH3:3])=[CH:5][C:6]([OH:21])=[CH:7][C:8]=3[CH:9]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22221615HCID 22221615, compound

Product 1

HCID 22221622HCID 22221622, compoundYield 338.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-Isopropyl-5-methoxy-2-(4-methoxy-phenyl)-benzofuran 117 (0.26 g, 0.88 mmol) and Pyridine HCl (5 g) wre heated to 200° C. After 1 hr, the reaction was cooled, diluted with water and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated and the product was purified by column chromatography on silica gel (25% EtOAc/hexane) to give 118 as a solid (0.80 g, 34%): Mp=192-194° C.; 1H NMR (DMSO-d6) δ 9.81 (br s, 1 H), 9.03 (br s, 1 H), 7.68 (d, 2 H, J=8.2 Hz), 6.98 (s, 1 H), 6.86 (d, 2H, J=8.1 Hz), 6.69 (d, 1 H, J=1.4 Hz), 6.54 (d, 1 H, J=1.9 Hz), 3.31 (m, 1 H), 1.32 (d, 6 H, J=6.9 Hz); MS 269 (M+H)+

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customthe product was purified by column chromatography on silica gel (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-26ecbaf2cbb7429ab37aee0f1701fe1e
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

Loading…