Tetrahydrofuran → (E)-4-[1,3]dioxolan-2-yl-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]butyric acid ethyl ester

HRID 1446495Notes

Reaction equation

HRID 1446495 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[N:16]1[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]1)[CH:11]=O.[CH2:22]([O:24][C:25](=[O:42])[CH:26](P(OCC)(OCC)=O)[CH2:27][CH2:28][CH:29]1[O:33][CH2:32][CH2:31][O:30]1)[CH3:23].O.[OH-].[Li+]>C(OCC)(=O)C.O>[CH2:22]([O:24][C:25](=[O:42])/[C:26](=[CH:11]/[C:10]1[CH:13]=[CH:14][C:15]([N:16]2[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]2)=[C:8]([O:7][CH3:6])[CH:9]=1)/[CH2:27][CH2:28][CH:29]1[O:33][CH2:32][CH2:31][O:30]1)[CH3:23]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 866024742-(Diethoxyphosphoryl)-4-[1,3]dioxolan-2-yl-butyric acid ethyl ester

Product 1

HCID 66961548(E)-4-[1,3]dioxolan-2-yl-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]butyric acid ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a THF (20 mL) solution of (1.75 g) of the 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde obtained in Example 1, 2-(diethoxyphosphoryl)-4-[1,3]dioxolan-2-yl-butyric acid ethyl ester (2.50 g) and lithium hydroxide monohydrate (388 mg) were added one by one, and the reaction solution was agitated at room temperature overnight. Water and ethyl acetate were added to the reaction solution after confirming disappearance of the starting materials, 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; heptane-ethyl acetate=1:2→ethyl acetate), and 1.05 g of the title compound as an isomer mixture (E:Z=4:1) was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (elution solvent; heptane-ethyl acetate=1:2→ethyl acetate), and 1.05 g of the title compound as an isomer mixture (E:Z=4:1)
  6. customwas obtained

Sources & evidence

ORD record
ord-96b536b63c5e47a2a61eb8bfeccdf53a
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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