Trifluoroacetic acid → HCID 11999708, compound

HRID 645915Notes

Reaction equation

HRID 645915 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2(O)[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[N:16]2[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:11][C:10]=1[O:34][CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=[O:24])[N:16]2[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:11][C:10]=1[O:34][CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68579670HCID 68579670, compound

Product 1

HCID 11999708HCID 11999708, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6 (0.50 g, 1.07 mmol), in CH2Cl2 (5 mL) at room temperature, trifluoroacetic acid (1.0 mL) was added and the reaction mixture was stirred for 6 h. Et3SiH (0.34 mL, 2.14 mmol) was added to the reaction mixture and the resulting pink solution was stirred overnight at room temperature. Solvent was evaporated under reduced pressure and the residue was neutralized with aqueous NaHCO3 solution and extracted with CH2Cl2 (2×10 mL). The combined organic layer was washed with H2O (5 mL), brine (5 mL) and then dried over anhydrous Na2SO4. Solvent was evaporated under reduced pressure and the residual light yellow syrup was purified by column chromatography using 20% acetone/hexane as the eluent to afford the title compound 8 (0.39 g, 81%) as a white solid.

Workup

  1. stirringthe resulting pink solution was stirred overnight at room temperature
  2. customSolvent was evaporated under reduced pressure
  3. extractionextracted with CH2Cl2 (2×10 mL)
  4. washThe combined organic layer was washed with H2O (5 mL), brine (5 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. customSolvent was evaporated under reduced pressure
  7. customthe residual light yellow syrup was purified by column chromatography

Sources & evidence

ORD record
ord-42f81ace0fc441399de1335c68a96031
Source dataset
uspto-grants-2010_04
Patent number
US07705021B2

Reaction notes

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