Potassium Carbonate → 1,1'-[Oxybis(methylene)]bis(4-methoxybenzene)

HRID 2374698Notes

Reaction equation

HRID 2374698 reaction equation
O[C:2]1[CH:3]=[C:4]2[C:10](=O)[O:9][C:8](=O)[C:5]2=N[CH:7]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1.[C:23](=O)([O-])[O-:24].[K+].[K+]>O1CCCC1>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:24][CH2:23][C:3]2[CH:2]=[CH:7][C:8]([O:9][CH3:10])=[CH:5][CH:4]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 59854183HCID 59854183, compound

Product 1

HCID 2211761,1'-[Oxybis(methylene)]bis(4-methoxybenzene)

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

For example, 3-hydroxy-furo[3,4-b]pyridine-5,7-dione 28.11 (German Patent 4343923) is reacted in tetrahydrofuran solution at 50° with 4-methoxybenzyl bromide and potassium carbonate, to give the 4-methoxybenzyl ether 28.12. The product is then converted, as described above, into the silyl-protected bicyclic ester 28.13. The 4-methoxybenzyl ether is then removed by reaction with dichlorodicyanobenzoquinone in dichloromethane at ambient temperature, as described in Tet. Lett., 27,3651, 1986, to give the phenol 28.14. The product is then reacted in tetrahydrofuran solution with a dialkyl bromomethyl phosphonate 29.15 (Lancaster) and potassium carbonate, to produce the phosphonate 28.16; the product is then converted, by desilylation, amide formation, bromination, reaction with methylamine and carbamate formation, using the procedures described above, into the hydroxyamide 28.17.

Sources & evidence

ORD record
ord-ba9baa73f406479988740b836ff2c17f
Source dataset
uspto-grants-2008_12
Patent number
US07462721B2

Reaction notes

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