Lithium hydroxide, monohydrate → tert-butyl(E)-5-chloro-2-{1-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene}valerate

HRID 1436138Notes

Reaction equation

HRID 1436138 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1)[CH:5]=O.[Cl:16][CH2:17][CH2:18][CH2:19][CH:20](P(OCC)(OCC)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].O.[OH-].[Li+].O.C(=O)(O)[O-].[Na+]>C1COCC1.C(O)C>[Cl:16][CH2:17][CH2:18][CH2:19]/[C:20](=[CH:5]\[C:4]1[CH:7]=[CH:8][C:9]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[C:2]([F:1])[CH:3]=1)/[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 168937Lithium hydroxide, monohydrateHCID 707008423-Fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86585896Sodium bicarbonate waterHCID 86602480Tert-butyl 5-chloro-2-(diethoxyphosphoryl)valerate

Product 1

HCID 69004836tert-butyl(E)-5-chloro-2-{1-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]methylidene}valerateYield 46.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (2.29 g) and tert-butyl 5-chloro-2-(diethoxyphosphoryl)valerate (3.68 g) were dissolved in a mixed solvent of THF (30 mL) and ethanol (10 mL). Lithium hydroxide monohydrate (1.41 g) was added to the reaction solution at room temperature, and the reaction solution was stirred at room temperature for 18 hours. Saturated sodium bicarbonate water was added to the reaction solution, followed by extraction with ethyl acetate. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system), solidified with tert-butyl methyl ether and heptane, and separated by filtration to obtain 1.96 g of the title compound. The property values of the compound are as follows.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe resulting extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)
  6. customseparated by filtration

Sources & evidence

ORD record
ord-e4245d1eb6c94ba9994356168e0a6688
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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