Hydrochloric Acid → HCID 86605897, compound

HRID 2221978Notes

Reaction equation

HRID 2221978 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:37])=[C:9]([CH2:11][O:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][O:18][C:19]3[C:24]([CH:25]=O)=[CH:23][N:22]=[C:21]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:20]=3)=[CH:15][C:14]=2[O:35][CH3:36])[N:10]=1.[CH2:38](P(=O)(OCC)OCC)[P:39](=[O:46])([O:43][CH2:44][CH3:45])[O:40][CH2:41][CH3:42].[H-].[Na+].Cl>O.CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:37])=[C:9]([CH2:11][O:12][C:13]2[CH:34]=[CH:33][C:16]([CH2:17][O:18][C:19]3[C:24](/[CH:25]=[CH:38]\[P:39](=[O:46])([O:43][CH2:44][CH3:45])[O:40][CH2:41][CH3:42])=[CH:23][N:22]=[C:21]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:20]=3)=[CH:15][C:14]=2[O:35][CH3:36])[N:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 15455Tetraethyl methylenediphosphonateHCID 24758Sodium hydrideHCID 86605890HCID 86605890, compound

Product 1

HCID 86605897HCID 86605897, compoundYield 7.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-2-phenylpyrimidine-5-carbaldehyde (1.00 g), tetraethyl methylenediphosphonate (0.58 g) and N,N-dimethylformamide (20 mL) was added sodium hydride (60% in oil, 0.090 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, 2N hydrochloric acid was added to acidify the solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography and eluted with acetone-hexane (2:3, v/v) to give diethyl (Z)-2-(4-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-2-phenylpyrimidin-5-yl)ethenylphosphonate as crystals (0.095 g, yield 7%). Recrystallization from acetone-hexane gave colorless needle crystals. melting point: 154-155° C.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with acetone-hexane (2:3

Sources & evidence

ORD record
ord-dd675308d4f54dea83fe28a7b9b0dd23
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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