Triphenylphosphine → HCID 68420767, compound

HRID 495190Notes

Reaction equation

HRID 495190 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[O:21][C:22]1[C:23]([C:35](=[O:44])[C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[C:24]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1>O1CCCC1.C(O)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:21][C:22]1[C:23]([C:35](=[O:44])[C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)=[C:24]([CH2:30][C:31]([O:33][CH3:34])=[O:32])[CH:25]=[C:26]([O:28][CH3:29])[CH:27]=1

Participants

6

Reactant 2

HCID 11776TriphenylphosphineHCID 23116354HCID 23116354, compound

Product 1

HCID 68420767HCID 68420767, compoundYield 56.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 284Formic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (0.22 g, 0.84 mmol) and palladium (II) acetate (47 mg, 0.21 mmol) were dissolved in tetrahydrofuran (2.0 mL) in an atmosphere of argon, followed by stirring at room temperature for 10 minutes. To the reaction mixture was added a solution of methyl 3,5-dimethoxy-2-(4-methoxybenzoyl)phenylacetate (0.78 g, 2.1 mmol) obtained in Example 26, Step 1 in formic acid (20 mL), followed by stirring at 80° C. for 5 hours. The reaction mixture was cooled to room temperature and then concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/1) to obtain Compound 27 (0.39 g, 56%).

Workup

  1. stirringby stirring at 80° C. for 5 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/4-1/1)

Sources & evidence

ORD record
ord-d9b871c80f4f4894b20ade230aaeb43d
Source dataset
uspto-grants-2009_05
Patent number
US07538224B2

Reaction notes

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