Methanesulfonic Acid → 5-(4-Methoxyphenyl)-2,2-dimethyl-4-(4-((5-methylpyridin-2-yl)methoxy)phenyl)furan-3(2H)-one methanesulfonate

HRID 1842426Notes

Reaction equation

HRID 1842426 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16](=[O:21])[C:15]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=3)=[CH:24][CH:23]=2)=[CH:10][CH:9]=1>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:18][C:17]([CH3:20])([CH3:19])[C:16](=[O:21])[C:15]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][N:31]=3)=[CH:24][CH:23]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 595801125-(4-methoxyphenyl)-2,2-dimethyl-4-(4-((5-methylpyridin-2-yl)methoxy)phenyl)furan-3(2H)-one

Product 1

HCID 866476615-(4-Methoxyphenyl)-2,2-dimethyl-4-(4-((5-methylpyridin-2-yl)methoxy)phenyl)furan-3(2H)-one methanesulfonateYield 90.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (462 mg, 4.8 mmol) was added to a solution of 5-(4-methoxyphenyl)-2,2-dimethyl-4-(4-((5-methylpyridin-2-yl)methoxy)phenyl)furan-3(2H)-one (2.0 g, 4.8 mmol) in DCM (5 ml) and diethyl ether (50 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 4 h upon which the solids were collected by filtration, washed with 20% DCM in diethyl ether and dried in vacuo to afford 5-(4-Methoxyphenyl)-2,2-dimethyl-4-(4-((5-methylpyridin-2-yl)methoxy)phenyl)furan-3(2H)-one methanesulfonate (2.0 g, 90.9%,) as a white solid. 1H NMR: 200 MHz, DMSO-d6: δ 8.5 (s, 1H), 7.6 (d, 1H), 7.55 (d, 2H), 7.4 (d, 1H), 7.2 (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: (99.3%, Condition-A).

Workup

  1. filtrationwere collected by filtration
  2. washwashed with 20% DCM in diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a8ee0968b95d4dd0bbf1b6ec26ba286f
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

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