Trifluoroacetic acid → HCID 23031084, compound

HRID 1766681Notes

Reaction equation

HRID 1766681 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:31])[C:5]([O:11][C:12]2[C:13]([CH2:29]O)=[C:14]([CH:26](O)[CH3:27])[C:15]([O:18]CC3C=CC=CC=3)=[CH:16][CH:17]=2)=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]1[CH:3]=[C:4]([CH3:31])[C:5]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:26][CH3:27])[C:13]=2[CH3:29])=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 23031267HCID 23031267, compound

Product 1

HCID 23031084HCID 23031084, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[-(7-amino-5-methylindan-4-yloxy)-6-benzyloxy-2-hydroxymethylphenyl]ethanol (40 mg) in dichloromethane (1 mL) was added triethylsilane (0.400 mL). Adding dropwise trifluoroacetic acid (1 mL), the mixture was stirred at room temperature overnight. The reaction mixture was evaporated to dryness. To the residue were added ethyl acetate (3 mL) and a saturated aqueous solution of sodium hydrogen carbonate (10 mL). The reaction mixture was stirred for 15 min, and extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=1/1) to give the title compound (24 mg).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionTo the residue were added ethyl acetate (3 mL)
  3. stirringThe reaction mixture was stirred for 15 min
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was purified by thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-765377beaea64083ba52a486af6a256a
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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