Potassium Bromide → HCID 86662610, Verbindung

HRID 1911983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911983
[C:1]([C:3]([CH3:12])([CH2:9][S:10][CH3:11])[C:4]([O:6]CC)=[O:5])#[N:2].[K+].[Br-]>CO>[C:1]([C:3]([CH3:12])([CH2:9][S:10][CH3:11])[C:4]([OH:6])=[O:5])#[N:2]

Komponenten

4

Edukt 2

HCID 253877Potassium BromideHCID 86662609HCID 86662609, Verbindung

Produkt 1

HCID 86662610HCID 86662610, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Ethyl 2-cyano-2-methyl-3-methylsulfanyl-propanoate (2.3 g, 12.3 mmol) was added to ice-cold sodium hydroxide (5 mL, 2N) under stirring. Methanol (10 mL) was added and the ice bath removed after an hour. After 45 minutes at room temperature, volatiles were removed under reduced pressure and the residue diluted with water (20 mL). Impurities were removed by ether extraction (2×30 mL). The aqueous layer was cooled in ice, acidified to pH 3 with dilute HCl and extracted with ethyl acetate (3×30 mL). Combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to leave a brown gum. Yield 1.32 g (68%): IR (KBr thin film) 1735 cm−1; 1H NMR (400 MHz, CDCl3) δ 10.19 (br, 1H), 3.10 (d, J=14.2 Hz, 1H), 2.94 (d, J=13.9 Hz, 1H), 2.33 (s, 3H), 1.73 (s, 3H); 13C NMR (400 MHz, CDCl3) δ 173.33, 118.82, 45.86, 41.66, 23.05, 17.62.

Aufarbeitung

  1. customthe ice bath removed after an hour
  2. customvolatiles were removed under reduced pressure
  3. additionthe residue diluted with water (20 mL)
  4. customImpurities were removed by ether extraction (2×30 mL)
  5. temperatureThe aqueous layer was cooled in ice
  6. extractionextracted with ethyl acetate (3×30 mL)
  7. dry with materialCombined organic extracts were dried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customto leave a brown gum

Quellen und Nachweise

ORD-Eintrag
ord-828d3cbadc8f4df8be6cb87c8c50a7ce
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604211B2

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