Fluoride Ion → HCID 178470429, compound

HRID 2097676Notes

Reaction equation

HRID 2097676 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:18][C:19](=[O:24])[CH2:20][N+:21]([O-])=O)[CH3:17].[Si]([N:29]=[N+:30]=[N-])(C)(C)C.[F-]>C1COCC1>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[C:10]1[N:29]=[N:30][NH:21][C:20]=1[C:19]([O:18][CH2:16][CH3:17])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 28179Fluoride IonHCID 69379Ethyl nitroacetateHCID 78378AzidotrimethylsilaneHCID 88060o-Phenoxybenzaldehyde

Product 1

HCID 178470429HCID 178470429, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-phenoxybenzaldehyde (8) (1.0 equiv), ethyl-2-nitroacetate (2.0 equiv) and TMS-azide (3.0 equiv) in dry THF (0.4 M) under inert atmosphere and at 0° C. was treated with fluoride-bound resin (Aldrich #387789, 1:1 w/w with respect to aldehyde). The resulting mixture was heated to reflux for 24 hours, cooled to room temperature and concentrated in vacuo. The residue was purified by flash chromatography (hexane/ethyl acetate) to provide ethyl 4-(2-phenoxyphenyl)-1H-1,2,3-triazole-5-carboxylate (9) as a yellow foam.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 24 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5ae1d8815aed469db09fd8d5c49ef952
Source dataset
uspto-grants-2013_05
Patent number
US08450350B2

Reaction notes

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