Pyridinium chloride → HCID 22221622, compound

HRID 1794534Notes

Reaction equation

HRID 1794534 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) were 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, 2 H, 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-c8c94f83767a4e638f7eda2363a0569f
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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