Triethylamine → HCID 22038559, compound

HRID 1581791Notes

Reaction equation

HRID 1581791 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 ethylacetate, 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 ethylacetate
  6. customthe organic layer is dried
  7. concentrationconcentrated
  8. customThe residue is purified by chromatography (toluene/ethanol 9:1)

Sources & evidence

ORD record
ord-81fd462c0e084c94aac34f6e94da2cbb
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

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