Triethylamine → HCID 22038559, compound

HRID 1790045Notes

Reaction equation

HRID 1790045 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH:4]=1)=O.C([N:17](CC)CC)C.Cl.NO>C(OC(=O)C)(=O)C>[C:1]([C:3]1[CH:7]=[CH:6][N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[OH:14])[CH:4]=1)#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 116080562-(3-Formyl-1-pyrrolyl)phenol

Product 1

HCID 22038559HCID 22038559, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

2-(3-Formyl-1-pyrrolyl)phenol (3 g, 16 mmol) and triethylamine (17.6 mmol) are added to a suspension of hydroxylamine hydrochloride (1.22 g, 17.6 mmol) in acetic anhydride (7.7 ml), and the mixture is allowed to stir overnight at ambient temperature. The mixture is refluxed for 5 hours, concentrated, dissolved in 50 ml ethanol and stirred for 10 min with 50 ml 2 M aqueous sodium hydroxide. After neutralisation with aqueous hydrochloric acid, and extraction with ethyl acetate, the organic layer is dried and concentrated. The residue is purified by chromatography (toluene/ethanol 9:1) to yield 2-(3-cyano-1-pyrrolyl)phenol (2.4 g, 92%). This phenolic product is reacted with (2S)-glycidyl 3-nitrobenzenesulfonate substantially as described for Epoxide 1 to yield the title epoxide.

Workup

  1. temperatureThe mixture is refluxed for 5 hours
  2. concentrationconcentrated
  3. dissolutiondissolved in 50 ml ethanol
  4. stirringstirred for 10 min with 50 ml 2 M aqueous sodium hydroxide
  5. extractionAfter neutralisation with aqueous hydrochloric acid, and extraction with ethyl acetate
  6. customthe organic layer is dried
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography (toluene/ethanol 9:1)

Sources & evidence

ORD record
ord-25102b621b5e4d25a5e2652806a36518
Source dataset
uspto-grants-2006_07
Patent number
US07071208B2

Reaction notes

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