Sodium hydride → HCID 86714714, compound

HRID 529226Notes

Reaction equation

HRID 529226 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:18])[CH2:9]P(OCC)(OCC)=O)([CH3:6])([CH3:5])[CH3:4].[CH2:19]([O:26][C:27]([C:29]1[S:30][C:31]([CH:34]=O)=[CH:32][CH:33]=1)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1.C(OCC)(=O)C>[CH2:19]([O:26][C:27]([C:29]1[S:30][C:31]([CH:34]=[CH:9][C:8]([O:7][C:3]([CH3:4])([CH3:5])[CH3:6])=[O:18])=[CH:32][CH:33]=1)=[O:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 2773685tert-Butyl diethylphosphonoacetateHCID 86714708HCID 86714708, compound

Product 1

HCID 86714714HCID 86714714, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 60% sodium hydride (1.64 g, 41 mmol) in tetrahydrofuran (50 ml) was added dropwise diethylphosphonoacetic acid tert-butyl ester (12.0 g, 47.6 mmol) at 0° C. After stirring at room temperature for 20 minutes, a solution of 5-formyl-2-thiophenecarboxylic acid benzyl ester (8.75 g, 35.5 mmol) in tetrahydrofuran (10 ml) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, and washed successively with 1N hydrochloric acid and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated and the residue was purified by column chromatography (10 to 30% ethyl acetate/hexane mixed solvent) to give the title compound (10.6 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. washwashed successively with 1N hydrochloric acid and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customthe residue was purified by column chromatography (10 to 30% ethyl acetate/hexane mixed solvent)

Sources & evidence

ORD record
ord-008002d94a3a4085ab3327b8b559d94e
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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