Potassium Carbonate → HCID 11149373, compound

HRID 1470791Notes

Reaction equation

HRID 1470791 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](=[O:13])([O-])[O-:11].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.F[B-](F)(F)F.C1(P(C2CCCCC2)C2C(OC)=CC(OC)=CC=2OC)CCCCC1>[CH3:6][C:1]1[C:10](=[O:13])[O:11][C@@H:3]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:2]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 66827Phenylboronic Acid

Product 1

HCID 11149373HCID 11149373, compoundYield 160.6%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 86668671HCID 86668671, compoundCatalystHCID 1140TolueneSolvent

Procedure

This reaction is carried out in the same manner as the reaction in example 5. The difference is that, the reactans are (S)-3-methyl-4-chloride-5-phenyl-2(5H)— furanone (20.2 mg, 0.097 mmol), phenylboronic acid (19.0 mg, 98%, 0.15 mmol), palladium acetate (1.1 mg, 0.01 mmol), dicyclohexyl(2,4,6-trimethoxyphenyl)phosphine tetrafluoroborate (2.5 mg, 0.0055 mmol), potassium carbonate (62.3 mg, 0.45 mmol) are reacted in 2 mL of anhydrous toluene at 110° C. for 6 minutes and 20.1 mg (S)-3-methyl-4,5-diphenyl-2(5H)-furanone is obtained. The yield is 83%, 99% ee.

Workup

  1. customThis reaction is carried out in the same manner as the reaction in example 5

Sources & evidence

ORD record
ord-40d24ad42e154c69b7208e389c7b1af3
Source dataset
uspto-grants-2015_04
Patent number
US09006491B2

Reaction notes

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