Triethylamine → HCID 22038559, compound

HRID 852211Notes

Reaction equation

HRID 852211 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-4971f6076dad4770a7dd392d54aa2705
Source dataset
uspto-grants-2007_08
Patent number
US07253181B2

Reaction notes

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