HCID 15461787, compound → HCID 15461788, compound

HRID 566437Notes

Reaction equation

HRID 566437 reaction equation
[CH2:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH2:19][O:20][CH3:21])=[C:8]([CH2:22][OH:23])[N:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]>C1(C)C=CC=CC=1.[O-2].[Mn+2]>[CH2:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH2:19][O:20][CH3:21])=[C:8]([CH:22]=[O:23])[N:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 15461787HCID 15461787, compound

Product 1

HCID 15461788HCID 15461788, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 1140TolueneSolvent

Procedure

To a solution 1-n-butyl-4-hydroxymethyl-5-(2-methoxymethoxy-4-methoxy-phenyl)-1H-imidazole (0.05 g, 0.16 mmol) in toluene (5 mL) was added manganese oxide (0.04 g, 0.47 mmol). The mixture was stirred for 5 h at room temperature. The mixture was filtered and the filtrate was evaporated to dryness. Flash column chromatography (1:4 ethyl acetate/hexane) of the residue afforded the title compound as an oil (0.05 g, 94%). 1H NMR (250 MHz, CDCl3) δ 9.65 (s, 1H), 7.58 (s, 1H), 7.13 (d, 1H), 6.80 (d, 1H), 6.65 (dd, 1H), 5.05 (s, 2H), 3.90 (s, 3H) 3.80 (t, 2H), 3.35 (s, 3H), 1.55 (quintet, 2H), 1.25 (quintet, 2H), 0.83 (t, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-96d73086cab84bd0b4b6018a71d8d7c2
Source dataset
uspto-grants-2001_01
Patent number
US06174906B1

Reaction notes

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