Triethyl phosphonoacetate → HCID 21473739, compound

HRID 742308Notes

Reaction equation

HRID 742308 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH:17]([C:19]1[S:23][C:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:20]=1)=O>CCCCCC.O1CCCC1.C(OCC)C>[CH2:15]([O:14][C:12](/[CH:11]=[CH:17]/[C:19]1[S:23][C:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:20]=1)=[O:13])[CH3:16]

Participants

7

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 21473735tert-Butyl 5-formylthiophene-2-carboxylate

Product 1

HCID 21473739HCID 21473739, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

Sodium hydride (min 60% paraffinic dispersion, 1.88 g, about 47 mmol) was washed with anhydrous hexane in a nitrogen stream and suspended in anhydrous tetrahydrofuran. The obtained suspension was stirred under cooling with ice, followed by the gradual dropwise addition of a solution of ethyl diethylphosphonoacetate (10.53 g, 47 mmol) in anhydrous tetrahydrofuran. The obtained mixture was stirred at room temperature for 15 minutes. A solution of the t-butyl 5-formyl-2-thiophenecarboxylate (6.65 g, 31.3 mmol) prepared above in anhydrous tetrahydrofuran was gradually dropped into the resulting mixture under cooling with ice. The obtained mixture was stirred at room temperature for 30 minutes, diluted with diethyl ether, washed with a dilute alkali, diluted hydrochloric acid and an aqueous solution of common salt, dehydrated and evaporated in a vacuum to dryness. The residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=8:1) to give the objective compound. yield: 7.58 g

Workup

  1. temperatureunder cooling with ice
  2. stirringThe obtained mixture was stirred at room temperature for 15 minutes
  3. additionwas gradually dropped into the resulting mixture
  4. temperatureunder cooling with ice
  5. stirringThe obtained mixture was stirred at room temperature for 30 minutes
  6. washwashed with a dilute alkali, diluted hydrochloric acid
  7. customevaporated in a vacuum to dryness
  8. customThe residue was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=8:1)
  9. customto give the objective compound

Sources & evidence

ORD record
ord-8569fc7ae7484a12bb1f9a0615ac6a73
Source dataset
uspto-grants-1996_09
Patent number
US05554615

Reaction notes

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