Azido(trimethyl)stannane → HCID 178497409, Verbindung

HRID 391394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 391394
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:13][CH3:14])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[N:15]([Sn](C)(C)C)=[N+:16]=[N-:17]>C1(C)C=CC=CC=1>[CH3:14][O:13][C:6]1[CH:5]=[CH:4][C:3]([C:1]2[NH:17][N:16]=[N:15][N:2]=2)=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Komponenten

4

Edukt 2

HCID 5104973Azido(trimethyl)stannaneHCID 18464789Methyl 5-cyano-2-methoxybenzoate

Produkt 1

HCID 178497409HCID 178497409, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A stirred solution of methyl 5-cyano-2-methoxybenzoate (0.87 g, 4.5 mmol) in toluene (4 mL) was treated with azidotrimethyltin (1.85 g, 9.0 mmol) and heated at reflux overnight. After cooling to room temperature, the solvents were evaporated. The crude product was dissolved in ethyl acetate, washed with brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (5% methanol/methylene chloride) afforded 0.78 g (75%). LC/MS (HPLC method 3): tR=1.66 min, 235.05 (MH)+.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customthe solvents were evaporated
  4. dissolutionThe crude product was dissolved in ethyl acetate
  5. washwashed with brine (2×)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customColumn chromatography on silica gel (5% methanol/methylene chloride) afforded 0.78 g (75%)

Quellen und Nachweise

ORD-Eintrag
ord-a904a4865e644c39bf9be521b7a19957
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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