Water → HCID 11448956, compound

HRID 1428171Notes

Reaction equation

HRID 1428171 reaction equation
[H-].[Na+].[H][H].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2[CH:19]=O)=[CH:9][CH:8]=1.[OH2:21].[O:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][C:14]=2/[CH:19]=[CH:24]/[C:23]([O:22][CH2:26][CH3:25])=[O:21])=[CH:11][CH:12]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 11031182404338-70-1HCID 178418361HCID 178418361, compound

Product 1

HCID 11448956HCID 11448956, compound

Procedure

To a mixture of sodium hydride (60% in oil, 0.71 g) and dry tetrahydrofuran (25 mL) was slowly added triethyl phosphonoacetate (3.63 g) under ice-cooling, and the mixture was stirred until completion of the generation of hydrogen gas. To the reaction mixture was slowly added a solution of 4-(4-methoxyphenyl)pyridine-3-carbaldehyde (2.88 g) in dry tetrahydrofuran (5 mL) under ice-cooling, and the mixture was stirred for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate) to give the title compound (2.85 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate)

Sources & evidence

ORD record
ord-5273d8395ad34547a30761ed1e884d16
Source dataset
uspto-grants-2015_01
Patent number
US08937055B2

Reaction notes

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