Pyridine → HCID 22054220, compound

HRID 1830237Notes

Reaction equation

HRID 1830237 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:27])=[C:5]([C:18]([O:25][CH3:26])=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:27])=[C:5]([C:18]([O:25][CH3:26])=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:17][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 21919163HCID 21919163, compound

Product 1

HCID 22054220HCID 22054220, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoate (0.510 g, 1.18 mmol) was dissolved in methylene chloride (12 ml) and after adding thereto in sequence copper acetate (0.215 g, 1.18 mmol), phenylboronic acid (0.289 g, 2.37 mmol), Molecular Sieves 4A (0.300 g), triethylamine (0.299 g, 2.96 mmol) and pyridine (0.234 g, 2.96 mmol), the solution was stirred at room temperature for 12 hours. The reaction solution was filtered and the filtrate was poured into water and then extracted with methylene chloride. The extract was washed with saturated brine, then dried and concentrated. The obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=3:1) to obtain the titled compound (0.220 g, 0.487 mmol, 41%).

Workup

  1. additionafter adding
  2. filtrationThe reaction solution was filtered
  3. additionthe filtrate was poured into water
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe obtained residue was purified by silica gel column chromatography (hexand:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-ab3333acf39e4b4583cce5c1d17b29bd
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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