Ethyl Acetate → HCID 14529703, compound

HRID 973701Notes

Reaction equation

HRID 973701 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)=[CH:5][C:4]=1OS(C(F)(F)F)(=O)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][NH:12][C:11](=[O:14])[CH2:10]2)=[CH:5][C:4]=1[C:29]1[CH:28]=[CH:27][CH:26]=[C:25]([O:24][CH3:23])[CH:30]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 14529698HCID 14529698, compound

Product 1

HCID 14529703HCID 14529703, compoundYield 62.9%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution is prepared from 339 mg of 4-(4-methoxy-3-trifluoromethanesulfonyloxyphenyl)-pyrrolidin-2-one in 9 ml of toluene and 4 ml of ethanol and stirred for 5 minutes under argon at room temperature with 38 mg of tetrakis(triphenylphosphine) palladium(0). After addition of 172 mg of m-methoxyphenylboronic acid and 1.3 ml of 2-molar sodium carbonate solution, the mixture is heated to 90° C. for 4 hours. After adding ethyl acetate and water, the organic phase is separated, washed neutral with saturated sodium chloride solution, dried over sodium sulfate, and concentrated. Recrystallization from alcohol/ethyl acetate/petroleum ether (40°-60° C.) yields 187 mg of compound having a melting point of 137°-139° C.

Workup

  1. customthe organic phase is separated
  2. washwashed neutral with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customRecrystallization from alcohol/ethyl acetate/petroleum ether (40°-60° C.)

Sources & evidence

ORD record
ord-dc012e7d575447878d7e7c1842fca8b3
Source dataset
uspto-grants-1991_11
Patent number
US05064854

Reaction notes

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