Tetrahydrofuran → tert-butyl 1H-pyrrole-3-carboxylate

HRID 1748476Notes

Reaction equation

HRID 1748476 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].C1(C)C(S([N:19]=C=O)(=O)=O)=CC=CC=1.[H-].[Na+].O1[CH2:29][CH2:28]CC1>>[C:6]([O:5][C:1]([C:2]1[CH:29]=[CH:28][NH:19][CH:3]=1)=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 15458tert-Butyl acrylateHCID 24758Sodium hydrideHCID 2733313o-Toluenesulfonyl Isocyanate

Product 1

HCID 11171190tert-butyl 1H-pyrrole-3-carboxylate

Procedure

A solution of tert-butyl acrylate (10.5 g) and toluenesulfonylisocyanate (16 g) in tetrahydrofuran (210 ml) was added dropwise at 70° C. to a suspension of sodium hydride (3.9 g) in tetrahydrofuran (200 ml) over 0.5 hour and stirred at the same temperature for two hours. After completion of the reaction, the solvent was evaporated, water was added to the residue and extracted with ethyl acetate three times. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) and recrystallized (n-hexane/ethyl acetate) to give the titled compound (5.27 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. additionwater was added to the residue
  4. extractionextracted with ethyl acetate three times
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)
  8. customrecrystallized (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-94cac7eaba6346a587b9523025f28284
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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