Methanesulfonic Acid → 4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate

HRID 1842404Notes

Reaction equation

HRID 1842404 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]1[C:8]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23](=[O:37])[C:24]([CH3:36])([CH3:35])[O:25][C:26]=3[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[CH:18][CH:17]=2)=[N:9][CH:10]=[C:11]([CH3:13])[CH:12]=1>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][C:7]1[C:8]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[C:23](=[O:37])[C:24]([CH3:35])([CH3:36])[O:25][C:26]=3[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)=[CH:20][CH:21]=2)=[N:9][CH:10]=[C:11]([CH3:13])[CH:12]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 595801614-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

Product 1

HCID 866476554-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonateYield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (445.0 mg, 4.6 mmol) was added to a solution of 4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (2.01 g, 4.6 mmol) in DCM (3 ml) and diethyl ether (150 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 4 h and the solids were removed by filtration. The solid was washed with 20% DCM in diethyl ether and dried under vacuo to afford 4-(4-((3,5-dimethylpyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate (2.1 g, 87%) as a white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.2 (s, 1H), 7.65 (d, 2H), 7.45 (s, 1H), 7.15 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 5.2 (s, 2H), 3.8 (s, 3H), 2.35 (s, 3H), 2.3 (s, 3H), 1.45 (s, 6H), HPLC: (98.9%, Condition-A).

Workup

  1. customthe solids were removed by filtration
  2. washThe solid was washed with 20% DCM in diethyl ether
  3. customdried under vacuo

Sources & evidence

ORD record
ord-5471ab5c254f410d9b3838264265482b
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

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