Ethanol → HCID 24780589, compound

HRID 553933Notes

Reaction equation

HRID 553933 reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1)[CH:8]=O.[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[C@H:27]1[N:35]2[C@@H:30]([CH2:31][CH2:32][CH:33](P(=O)(OCC)OCC)[C:34]2=[O:36])[CH2:29][CH2:28]1.C(O)C>O1CCCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=1[C@H:27]1[N:35]2[C@@H:30]([CH2:31][CH2:32]/[C:33](=[CH:8]\[C:7]3[CH:10]=[CH:11][C:12]([N:13]4[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]4)=[C:5]([O:4][CH3:3])[CH:6]=3)/[C:34]2=[O:36])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 702EthanolHCID 3939Lithium HydroxideHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612707HCID 86612707, compound

Product 1

HCID 24780589HCID 24780589, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.443 g) was added to a mixed solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (1.0 g) and diethyl [(3S,8aR)-3-(2,5-difluorophenyl)-5-oxooctahydroindolizin-6-yl]phosphonate (4.1 g) in tetrahydrofuran (4 mL)-ethanol (16 mL), and the reaction solution was stirred under shading at room temperature for 12 hours. The reaction solution was poured into ice water, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 1.85 g of the title compound as a colorless oil. The property values of the compound are as follows.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-e3fb91c99497413cae651d5fe4aaf085
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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