Trifluoroacetic acid → HCID 178419844, compound

HRID 1935752Notes

Reaction equation

HRID 1935752 reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH2:15]([CH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:32]2[N:33]=[CH:34][N:35](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:36]=2)(O)[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>ClCCl>[CH2:15]([CH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:32]2[N:33]=[CH:34][NH:35][CH:36]=2)=[CH:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22465367HCID 22465367, compound

Product 1

HCID 178419844HCID 178419844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylsilane (1 ml, 0.728 g, 6.26 mmol) and trifluoroacetic acid (1.9 ml, 2.81 g, 24.7 mmol) were added to the solution of 3-benzyl-1-(1-trityl-1H-imidazol-4-yl)indan-1-ol (0.387 g, 0.73 mmol) in dichloromethane (13 ml). The reaction was stirred at room temperature for 20 hr. Then the reaction was quenched with water and made basic with the 2 M sodium hydroxide solution. The dichloromethane layer was washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure. Flash chromatography using a dichloromethane-methanol gradient afforded 4-(3-benzyl-3H-inden-1-yl)-1H-imidazole.

Workup

  1. customThen the reaction was quenched with water
  2. washThe dichloromethane layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5f0f86800c5c45c49632361f99739d74
Source dataset
uspto-grants-2002_05
Patent number
US06388090B2

Reaction notes

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