HCID 15461787, compound → HCID 15461788, compound

HRID 378235Notes

Reaction equation

HRID 378235 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-methoxyphenyl)-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-c18ec05eb7fd403ba40c404e2f0ea3b0
Source dataset
uspto-grants-2000_02
Patent number
US06030970

Reaction notes

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