Water → HCID 66961085, compound

HRID 2247511Notes

Reaction equation

HRID 2247511 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1)[CH:6]=O.[CH2:17]([O:19][C:20](=[O:38])[CH:21](P(OCC)(OCC)=O)[CH2:22][CH2:23][CH2:24][CH:25]1[O:29][CH2:28][CH2:27][O:26]1)[CH3:18].O.[OH-].[Li+].O>C1COCC1.C(O)C.C(OCC)(=O)C>[CH2:17]([O:19][C:20](=[O:38])/[C:21](=[CH:6]/[C:5]1[CH:8]=[CH:9][C:10]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)=[C:3]([O:2][CH3:1])[CH:4]=1)/[CH2:22][CH2:23][CH2:24][CH:25]1[O:29][CH2:28][CH2:27][O:26]1)[CH3:18]

Participants

8

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86602476HCID 86602476, compound

Product 1

HCID 66961085HCID 66961085, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)-benzaldehyde (580 mg) obtained in Example 1 in THF (10 mL) and ethanol (10 mL), 2-(diethoxyphosphoryl)-5-[1,3]dioxolan-2-yl valeric acid ethyl ester (826 mg) and lithium hydroxide monohydrate (205 mg) were added one by one, and the reaction solution was agitated at room temperature overnight. After confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:ethanol=20:1), and it was obtained 485 mg, the title compound was obtained as an isomer mixture (E:Z=4:1). The physical properties of the compound are as follows.

Workup

  1. additionwere added to the reaction solution
  2. customthe organic layer was partitioned
  3. washAfter the obtained organic layer was washed with a saturated saline solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (elution solvent: ethyl acetate->ethyl acetate:ethanol=20:1)
  7. customit was obtained 485 mg

Sources & evidence

ORD record
ord-9b8bb3a3c8aa418e8a6d830955d16020
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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