Dichloromethane → (4,5-Dimethoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 416267Notes

Reaction equation

HRID 416267 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[CH3:22][O:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([CH:32]([C:34]2[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([O:44][CH3:45])[CH:35]=2)[OH:33])=[C:26]([N+:46]([O-:48])=[O:47])[CH:25]=1.C(Cl)Cl>CCOCC>[CH3:22][O:23][C:24]1[C:29]([O:30][CH3:31])=[CH:28][C:27]([C:32]([C:34]2[CH:35]=[C:36]([O:44][CH3:45])[C:37]([O:42][CH3:43])=[C:38]([O:40][CH3:41])[CH:39]=2)=[O:33])=[C:26]([N+:46]([O-:48])=[O:47])[CH:25]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724130Cornforth reagent2×HCID 11143380(4,5-Dimethoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol

Product 1

HCID 11036207(4,5-Dimethoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 41%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Powdered 4 Å molecular sieves (583 mg) and pyridinium dichromate (2.17 g, 5.77 mmol) were successively added to a stirred solution of intermediate 241 (1.46 g, 3.84 mmol) in of anhydrous DCM (38.5 mL) at 0° C. The mixture was stirred at rt for 15 h. More PDC (290 mg, 0.770 mmol) was added and the mixture was stirred for another 4 h, The diluted with ether and filtered through a celite pad. The filtrate was concentrated and the brown solid was purified by flash chromatography using EtOAc/DCM (7:93) affording the title compound 242 (551 mg, 41%) as a yellow solid. 1H NMR (CDCl3) δ (ppm): 7.72 (s, 1H), 6.99 (s, 2H), 6.86 (s, 1H), 4.06 (s, 3H), 4.00 (s, 3H), 3.93 (s, 3H), 3.84 (s, 6H). m/z: 378.4 (MH+).

Workup

  1. stirringthe mixture was stirred for another 4 h
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated
  4. customthe brown solid was purified by flash chromatography

Sources & evidence

ORD record
ord-6523c33d47484973b9ae2c8874e07e1d
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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