Potassium Carbonate → 3-Methyl-4,5-diphenylfuran-2(5H)-one

HRID 1470790Notes

Reaction equation

HRID 1470790 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2CCCCC2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]2C(OC)=C[CH:26]=[CH:25][C:24]=2OC)CCCCC1.[C:39](=[O:42])([O-])[O-:40].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:26][C:25]1[C:39](=[O:42])[O:40][CH:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:17]=2)[C:24]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Product 1

HCID 123762193-Methyl-4,5-diphenylfuran-2(5H)-oneYield 40%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

This reaction is carried out in the same manner as the reaction in example 5. The difference is that, the reactants are (R)-(−)-3-propyl-4-chloride-5-phenyl-2(5H)— furanone (22.9 mg, 0.097 mmol, 97% ee), phenylboronic acid (19.0 mg, 98%, 0.15 mmol), palladium acetate (1.1 mg, 0.005 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2.1 mg, 0.005 mmol), potassium carbonate (62.1 mg, 0.45 mmol) and 1 mL of anhydrous toluene. The reactants are reacted for 1 hours under 110° C., and 3-methyl-4,5-diphenyl-2(5H)-furanone is obtained. The yield is 40%, <16% ee, 11% the starting material is recycled.

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 5
  2. customThe reactants are reacted for 1 hours under 110° C.

Sources & evidence

ORD record
ord-103da1ebd7ce435690e469e79e96d0f9
Source dataset
uspto-grants-2015_04
Patent number
US09006491B2

Reaction notes

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