Sodium hydride → HCID 86714707, compound

HRID 529222Notes

Reaction equation

HRID 529222 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7]P(OCC)(OCC)=O)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[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:1]([O:5][C:6](=[O:16])/[CH:7]=[CH:34]/[C:31]1[S:30][C:29]([C:27]([O:26][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:28])=[CH:33][CH:32]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

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

Product 1

HCID 86714707HCID 86714707, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diethylphosphonoacetic acid tert-butyl ester (12 g, 48 mmol) was dissolved in tetrahydrofuran (50 ml), 60% sodium hydride (1.6 g, 41 mmol) was added at 0° C., and the mixture was stirred for 30 minutes. A solution of 5-formyl-2-thiophenecarboxylic acid benzyl ester (8.8 g, 36 mmol) in tetrahydrofuran (1 mL) was added to the reaction mixture, and the mixture was stirred at room temperature overnight. The solvent was evaporated, and the residue was partitioned between ethyl acetate and 1N hydrochloric acid, and the organic layer was washed successively with water and saturated brine. After drying over anhydrous magnesium sulfate, the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  4. washthe organic layer was washed successively with water and saturated brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-32e09f6e373540059e9ef8f5304e294c
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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