Tetrahydrofuran → HCID 54549583, compound

HRID 431505Notes

Reaction equation

HRID 431505 reaction equation
[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH:13]=O)=[CH:11][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCOP([O:23][C:24]([CH3:26])=[O:25])(OCC)=O.[H-].[Na+].O1CC[CH2:31][CH2:30]1>>[C:1]([O:5][C:6]([C:8]1[S:9][C:10]([CH:13]=[CH:26][C:24]([O:23][CH2:30][CH3:31])=[O:25])=[CH:11][CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 18353Acetyl diethyl phosphateHCID 24758Sodium hydrideHCID 21473735tert-Butyl 5-formylthiophene-2-carboxylate

Product 1

HCID 54549583HCID 54549583, compound

Conditions

Temperature
60 °C

Procedure

1.7 g (8 mmol) of the product obtained in step c) were dissolved in 5 ml of dry tetrahydrofuran. The solution was added dropwise to a mixture of 2.24 g (10 mmol) of diethyl phosphonoacetate and 440 mg sodium hydride (55% in paraffin oil) in 30 ml of dry tetrahydrofuran. The resulting mixture was stirred at 60° C. for 3 hours. After cooling to room temperature, the mixture was poured onto water/ethyl acetate. The organic phase was separated, washed with 10% aqueous citric acid and dried with anhydrous magnesium sulfate. After filtration, the solvents were removed to give 2.6 g of raw product. This material was purified by column chromatography (silica gel; ethyl acetate/n-heptane (1/5; v/v)). The fractions containing the title compound were combined and evaporated to give 1.2 g of a clear light yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was poured onto water/ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with 10% aqueous citric acid
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvents were removed
  8. customto give 2.6 g of raw product
  9. customThis material was purified by column chromatography (silica gel; ethyl acetate/n-heptane (1/5; v/v))
  10. additionThe fractions containing the title compound
  11. customevaporated

Sources & evidence

ORD record
ord-c44ab3a0878b4640885560b839129d3e
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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