Water → HCID 66960126, compound

HRID 1362657Notes

Reaction equation

HRID 1362657 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:34])[CH:21](P(OCC)(OCC)=O)[CH2:22][CH2:23][CH2:24][Cl:25])[CH3:18].O.[OH-].[Li+].O>C1COCC1.C(O)C.C(OCC)(=O)C>[CH2:17]([O:19][C:20](=[O:34])/[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][Cl:25])[CH3:18]

Participants

8

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86602479Ethyl 5-chloro-2-(diethoxyphosphoryl)pentanoate

Product 1

HCID 66960126HCID 66960126, compoundYield 44.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (5 g) obtained in Example 1 in THF (60 mL) and ethanol (20 mL), 5-chloro-2-(diethoxyphosphoryl)valeric acid ethyl ester (7.6 g) and lithium hydroxide monohydrate (2.9 g) 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. 3.76 g of the title compound was obtained by purifying the residue by silica gel chromatography (heptane: elution solvent: ethyl acetate=1:1), and re-crystallizing the obtained solid from a mixed solvent of ethyl acetate and hexane.

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

Sources & evidence

ORD record
ord-51e2f97402004c3fac3e750ce8d5f01a
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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