Potassium Carbonate → 3-methyl-4-(methoxyphenyl)-5-phenyl-2(5H)-furanone

HRID 1470792Notes

Reaction equation

HRID 1470792 reaction equation
COOB([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)O.C1(P(C2CCCCC2)[C:19]2[C:24]([O:25][CH3:26])=[CH:23][C:22](OC)=[CH:21][C:20]=2OC)CCCCC1.[C:37](=[O:40])([O-])[O-:38].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:11][C:6]1[C:37](=[O:40])[O:38][CH:8]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:7]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 46867875Dicyclohexyl(2,4,6-trimethoxyphenyl)phosphineHCID 53405446Methoxyphenyl boronic acid

Product 1

HCID 681537523-methyl-4-(methoxyphenyl)-5-phenyl-2(5H)-furanoneYield 100%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

This reaction is carried out in the same manner as the reaction in example 4. The difference is that 3-methyl-4-chloride-5-phenyl-2(5H)— furanone (42.0 mg, 0.2 mmol), methoxyphenyl boronic acid (46.5 mg, 97%, 0.3 mmol), palladium acetate (2.3 mg, 0.01 mmol), dicyclohexyl(2,4,6-trimethoxyphenyl)phosphine (7.3 mg, 0.02 mmol), potassium carbonate (82.3 mg, 0.6 mmol) are reacted in 1 mL of toluene at 110° C. for 35 minutes and 3-methyl-4-(methoxyphenyl)-5-phenyl-2(5H)— furanone is obtained. The yield is 100%.

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 4

Sources & evidence

ORD record
ord-27019d8a6598491fba6b665cb0cda4d5
Source dataset
uspto-grants-2015_04
Patent number
US09006491B2

Reaction notes

Loading…