Diethyl P-((4-methylphenyl)methyl)phosphonate → HCID 54379836, compound

HRID 414579

Reaction equation

HRID 414579 reaction equation
[CH:1]([C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=O.[CH3:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19]P(=O)(OCC)OCC)=[CH:17][CH:16]=1.C[O-].[Na+]>CN(C)C=O>[CH3:14][C:15]1[CH:29]=[CH:28][C:18]([CH:19]=[CH:1][C:3]2[S:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3050Diethyl P-((4-methylphenyl)methyl)phosphonateHCID 1770535-Phenylthiophene-2-carbaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 54379836HCID 54379836, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.52 gram (0.008 mole) of 2-formyl-5-phenylthiophene and 2.0 grams (0.00820 mole) of diethyl 4-methylbenzylphosphonate in 40 mL of N,N-dimethylformamide was added 0.53 gram (0.0098 mole) of sodium methoxide. The reaction mixture was stirred at room temperature for approximately 18 hours and then was quenched with 50 mL of an aqueous solution saturated with ammonium chloride. A precipitate formed and was collected by filtration. The filter cake was washed with water. The washed solid was purified by column chromatography on silica gel, eluting with chloroform:n-hexane (10:90) yielded 1.1 gram of 2-(4-methylphenyl)-1-(5-phenylthien-2-yl)ethene as a solid, m.p. 159°-160° C.

Workup

  1. customwas quenched with 50 mL of an aqueous solution saturated with ammonium chloride
  2. customA precipitate formed
  3. filtrationwas collected by filtration
  4. washThe filter cake was washed with water
  5. customThe washed solid was purified by column chromatography on silica gel
  6. washeluting with chloroform:n-hexane (10:90)

Sources & evidence

ORD record
ord-382f0be6e0c5411ea1930300a25ddc48
Source dataset
uspto-grants-1988_12
Patent number
US04792567

Linked notes

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