HCID 15461786, compound → HCID 15461787, compound

HRID 566436Notes

Reaction equation

HRID 566436 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]([C:22](OCC)=[O:23])[N:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[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]

Participants

4

Reactant 2

HCID 15461786HCID 15461786, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15461787HCID 15461787, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-n-butyl-5-(2-methoxymethoxy-4-methoxyphenyl)-1H-imidazole-4-carboxylate (0.06 g, 0.17 mmol) in THF (5 mL) was added LAH (0.20 mL) at room temperature. The mixture was stirred for 2 h. After an aqueous work up, extracting with ethyl acetate (3×20 mL), the combined organic extracts were washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash column chromatography (1:1 ethyl acetate/hexane) of the residue afforded the title compound as an oil (0.05 g, 96%). 1H NMR (400 MHz, CDCl3) δ 7.53 (s, 1H), 7.19 (d, 1H), 6.85 (d, 1H), 6.65 (dd, 1H), 5.05 (d, 2H), 4.41 (dd, 2H), 3.85 (s, 3H) 3.80 (t, 2H), 3.45 (s, 3H) 3.23 (b, 1H), 1.55 (quintet, 2H), 1.25 (quintet, 2H), 0.83 (t, 3H).

Workup

  1. extractionAfter an aqueous work up, extracting with ethyl acetate (3×20 mL)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customAfter removing the solvent under reduced pressure, flash column chromatography (1:1 ethyl acetate/hexane) of the residue

Sources & evidence

ORD record
ord-4a23b63db76e48b1ba4f534539000d29
Source dataset
uspto-grants-2001_01
Patent number
US06174906B1

Reaction notes

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