Water → Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoate

HRID 2182467Notes

Reaction equation

HRID 2182467 reaction equation
O.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5][C:4]1=[CH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>CCO.C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([CH2:13][C:4]2[C:3](=[O:2])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][CH:5]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 962WaterHCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

Product 1

HCID 22478819Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoateYield 59%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Water (0.2 ml) and RhCl3.H2O (7 mg, 0.034 mmol) was added to a suspension of compound 260 (200 mg, 0.680 mmol) in EtOH (2 ml) and CHCL3 (2 ml). The reaction mixture was stirred 16 h at 70° C. The reaction mixture was cooled down and diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2) to afford the title compound 261 (118 mg, 59%) as a white solid. 1H NMR: (DMSO) δ (ppm): 8.45 (s, 1H), 8.03 (dd, J=7.9, 1.8 Hz, 1H), 7.87 (d, J=8.4 Hz, 2H), 7.83-7.77(m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.50-7.43 (m3, 1H), 3.82 (s, 3H), 3.80 (s, 2H).

Workup

  1. temperatureThe reaction mixture was cooled down
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b04d146af7e84dd49cca32ac3768e3a0
Source dataset
uspto-grants-2005_05
Patent number
US06897220B2

Reaction notes

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