Trifluoroacetic acid → HCID 67279429, compound

HRID 1694590Notes

Reaction equation

HRID 1694590 reaction equation
[I:1][C:2]1[CH:51]=[CH:50][C:5]([O:6][CH:7]([CH2:29][O:30]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:8][O:9]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>ClCCl.CO>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH2:29][OH:30])[CH2:8][OH:9])=[CH:50][CH:51]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 67279307HCID 67279307, compound

Product 1

HCID 67279429HCID 67279429, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

Compound 2 (2.5 g, 3.21 mmol) was dissolved in dichloromethane (25 mL). A solution of trifluoroacetic acid and trifluoroacetic anhydride in dry dichloromethane (1.83 M; 50 mL) was added and the reaction was allowed to proceed for 15 min at RT. The mixture was cooled on ice-water bath, and it was made basic with triethylamine, poured into methanol and concentrated. Precipitation from the mixture of dichloromethane and petroleum ether gave the title compound. Yield was 86%. Mp. 90° C. 1H NMR (DMSO-d6): 7.57 (2H, d, J 8.9); 6.83 (2H, d, J 8.9); 4.81 (2H, t, J 5.8); 4.22 (1H, m); 3.54 (4H, m).

Workup

  1. temperatureThe mixture was cooled on ice-water bath
  2. concentrationconcentrated
  3. customPrecipitation
  4. additionfrom the mixture of dichloromethane and petroleum ether

Sources & evidence

ORD record
ord-443ec68430a94b13b069c96bde810f58
Source dataset
uspto-grants-2012_04
Patent number
US08158782B2

Reaction notes

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