Ethanol → HCID 66961736, compound

HRID 2247623Notes

Reaction equation

HRID 2247623 reaction equation
[OH-].[Li+].[Cl:3][CH2:4][CH2:5][O:6][CH:7](P(OCC)(OCC)=O)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1)[CH:28]=O.C(O)C>C1COCC1.C(OCC)(=O)C.O>[Cl:3][CH2:4][CH2:5][O:6]/[C:7](=[CH:28]\[C:27]1[CH:30]=[CH:31][C:32]([N:33]2[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]2)=[C:25]([O:24][CH3:23])[CH:26]=1)/[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

8

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86602493HCID 86602493, compound

Product 1

HCID 66961736HCID 66961736, compoundYield 17.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium hydroxide (52.1 mg) was added to a solution of tert-butyl 2-chloroethoxy-(diethoxyphosphoryl)acetate (240 mg) synthesized by a technique described in a document (see C. J. Moody et al., “Tetrahedron”, 1992, vol. 48, p. 3991, for example) and 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (173 mg) in a mixture of THF (5.0 mL) with ethanol (1.0 mL), and the reaction solution was stirred at room temperature for 2.5 hours. Water and ethyl acetate were added to the reaction solution and the organic layer was partitioned. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate system) to obtain 51 mg of the title compound.

Workup

  1. customsynthesized by a technique
  2. customthe organic layer was partitioned
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-ba9226a5bbd9478392a42f0f3d0f4981
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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