HCID 14520343, compound → HCID 178421897, compound

HRID 1194382Notes

Reaction equation

HRID 1194382 reaction equation
[CH3:1][C:2]1([CH3:39])[O:7][C:6]2[C:8]([CH:13]([C:15]3[N:16]=[CH:17][N:18](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:19]=3)O)=[CH:9][C:10]([CH3:12])=[CH:11][C:5]=2[CH2:4][O:3]1>CO.[Pd].C(OCC)C>[CH3:1][C:2]1([CH3:39])[O:7][C:6]2[C:8]([CH2:13][C:15]3[N:16]=[CH:17][NH:18][CH:19]=3)=[CH:9][C:10]([CH3:12])=[CH:11][C:5]=2[CH2:4][O:3]1

Participants

5

Reactant 1

HCID 14520343HCID 14520343, compound

Product 1

HCID 178421897HCID 178421897, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

9.45 g (0.0183 mole) of alpha-(2,2,6-trimethyl-4H-1,3-benzodioxin-8-yl)-1-triphenylmethyl-1H-imidazole-4-methanol (prepared in Example 1.C.6.), dissolved in 300 ml of methanol, are subjected to hyrogeolysis in the presence of 0.6 g of 10% palladium on carbon for 4 hours at 80° C., under a hydrogen pressure of 2 hours. The catalyst is then filtered off and the solvent removed. The residue obtained is stirred in diethyl ether to remove the triphenylmethane, then chromatographed on 700 g of silica (10 μm) (eluent: 95:5 v/v dichloromethane-methanol). A 60:40 mixture of 4-[(2,2,6-trimethyl-4H-1,3-benzodioxin-8-yl)(methoxy)methyl]-1H-imidazole and 4-[(2,2,6-trimethyl-4H-1,3-benzodioxin-8-yl)methyl]-1H-imidazole is isolated and identified by NMR by the presence of a peak corresponding to the methoxy radical (DMSO: delta 3.13). The mixture is used as such in the following step.

Workup

  1. custompressure of 2 hours
  2. filtrationThe catalyst is then filtered off
  3. customthe solvent removed
  4. customThe residue obtained
  5. customto remove the triphenylmethane
  6. customchromatographed on 700 g of silica (10 μm) (eluent: 95:5 v/v dichloromethane-methanol)
  7. additionA 60:40 mixture of 4-[(2,2,6-trimethyl-4H-1,3-benzodioxin-8-yl)(methoxy)methyl]-1H-imidazole

Sources & evidence

ORD record
ord-6bd6f389253f45e89dc507dc1539be05
Source dataset
uspto-grants-1989_03
Patent number
US04814343

Reaction notes

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