Trifluoroacetic acid → HCID 18786114, compound

HRID 1107875Notes

Reaction equation

HRID 1107875 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[C:17]([CH:18](O)[CH2:19][N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][CH:15]=[CH:14][C:6]=2[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[CH2:1]([C:3]1[O:4][C:5]2[C:17]([CH2:18][CH2:19][N:20]([CH2:21][CH3:22])[CH2:23][CH3:24])=[CH:16][CH:15]=[CH:14][C:6]=2[C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 11430Potassium CarbonateHCID 12052Triethylsilane2×HCID 15391859HCID 15391859, compound

Product 1

HCID 18786114HCID 18786114, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

180 mg (0.53 mmol) of 2-ethyl-3-phenyl-7-(2-diethylamino-1-hydroxyethyl)benzofuran, 1 ml of triethylsilane and 1 ml of trifluoroacetic acid are introduced into a 25 ml three-necked flask equipped with a reflux condenser. The mixture is stirred for 2 hours at room temperature and then 2 ml of triethylsilane and 1 ml of trifluoroacetic acid are added. The mixture is heated at 70° C. for 48 hours. Potassium carbonate and ethyl ether (30 ml) are added and the mixture is filtered. The filtrate is concentrated under vacuum and the residue is purified by silica column chromatography (elution solvent: 5% methanol in dichloromethane). 80 mg of 2-ethyl-3-phenyl-7-(2-(diethylamino)ethyl)benzofuran are obtained in the form of a wax.

Workup

  1. customequipped with a reflux condenser
  2. temperatureThe mixture is heated at 70° C. for 48 hours
  3. filtrationthe mixture is filtered
  4. concentrationThe filtrate is concentrated under vacuum
  5. customthe residue is purified by silica column chromatography (elution solvent: 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-282c9fcb94e041e2b80613c4bb76cd5c
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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