p-Toluenesulfonic acid → HCID 20083278, compound

HRID 1694810Notes

Reaction equation

HRID 1694810 reaction equation
F[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6](F)[C:3]=1[CH:4]=[O:5].[CH2:13](N)[CH2:14]CC.[C:18]1(C)C=CC(S(O)(=O)=O)=C[CH:19]=1.C([Mg]Br)C>C1(C)C=CC=CC=1.O1CCCC1.CCOCC.[Cl-].[Mn+2].[Cl-]>[CH2:13]([C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([CH2:18][CH3:19])[C:3]=1[CH:4]=[O:5])[CH3:14]

Participants

9

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8007ButylamineHCID 37037132,6-Difluoro-4-methoxybenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 20083278HCID 20083278, compound

Reagents, catalysts & solvents 4

HCID 10313134Manganese(2+) dichlorideCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared in analogy to Example 57(a)-(b) from 2,6-difluoro-4-methoxybenzaldehyde, N-butylamine and p-toluenesulphonic acid in toluene, then treatment with 3 equivalents of ethylmagnesium bromide and manganese(II) chloride in tetrahydrofuran and ether followed by chromatography on silical gel. MS (ISP): 193.3 ([M+H]+).

Sources & evidence

ORD record
ord-fb16f8ee2e4e489ebae47c2d9d52f00a
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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