Trifluoroacetic anhydride → Ethyl 7-oxo-1,4,5,6-tetrahydroindole-2-carboxylate

HRID 1026446Notes

Reaction equation

HRID 1026446 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:10][CH:9]=[C:8]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH:7]=1)=[O:5])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(O)(C(F)(F)F)=O>[O:16]=[C:14]1[C:9]2[NH:10][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][C:8]=2[CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 152728224-(5-(Ethoxycarbonyl)-1H-pyrrol-3-yl)butanoic acid

Product 1

HCID 848532Ethyl 7-oxo-1,4,5,6-tetrahydroindole-2-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Into a 1000-mL round-bottom flask was placed a solution of 113h (30 g, 133.19 mmol, 1.00 equiv) in CF3COOH (500 mL) and trifluoroacetyl 2,2,2-trifluoroacetate (42 g, 199.97 mmol, 1.50 equiv). See FIG. 14. The resulting solution was stirred at room temperature for 60 min, concentrated under vacuum, diluted with 500 mL of water and 500 mL of EA, and extracted with 3×500 mL of ethyl acetate. The combined organic layers were washed with 1×500 mL of saturated aqueous potassium carbonate and 1×500 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford 24 g (87%) of 113i as a light brown solid.

Workup

  1. customInto a 1000-mL round-bottom flask was placed
  2. concentrationconcentrated under vacuum
  3. additiondiluted with 500 mL of water and 500 mL of EA
  4. extractionextracted with 3×500 mL of ethyl acetate
  5. washThe combined organic layers were washed with 1×500 mL of saturated aqueous potassium carbonate and 1×500 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-05551128ae43406b911518153f48fc5a
Source dataset
uspto-grants-2014_05
Patent number
US08729072B2

Reaction notes

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