Trifluoroacetic acid → HCID 117687632, compound

HRID 920873Notes

Reaction equation

HRID 920873 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]([CH:26]=[O:27])=[CH:18]2)C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[OH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]=[O:27])=[CH:18]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 117687648HCID 117687648, compound

Product 1

HCID 117687632HCID 117687632, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2.6 g of 1-(2-(2-(2-triphenylmethoxyethoxy)ethoxy)ethyl)-1H-indole-3-carbaldehyde (5.0 mmol) in 50 mL dichloromethane is added 4.0 mL of triethylsilane (2.9 g, 25 mmol) followed by 4.0 mL of trifluoroacetic acid (5.5 g, 50 mmol). The solution is stirred at room temperature for 2 hrs and then washed 3×100 mL saturated NH4CO3. The solution is dried over anhydrous Na2SO4 and the solvent is removed via vacuum. The resultant residue is purified via column chromatography over alumina, eluting with a gradient of methanol in dichloromethane.

Workup

  1. washwashed 3×100 mL saturated NH4CO3
  2. dry with materialThe solution is dried over anhydrous Na2SO4
  3. customthe solvent is removed via vacuum
  4. customThe resultant residue is purified via column chromatography over alumina
  5. washeluting with a gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-e2dbb784d5df499091e74083c7e9c171
Source dataset
uspto-grants-2016_03
Patent number
US09273074B2

Reaction notes

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