HCID 15461786, compound → HCID 15461787, compound

HRID 378234Notes

Reaction equation

HRID 378234 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-fc65d58cd55c42d5a257d6a1150162d8
Source dataset
uspto-grants-2000_02
Patent number
US06030970

Reaction notes

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