Propanal → 5-Ethyl-4-tosyl-2-oxazoline

HRID 505573

Reaktionsgleichung

Reaktionsgleichung von HRID 505573
[S:1]([CH2:11][N:12]=[C:13]=[O:14])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH:15](=O)[CH2:16][CH3:17].[Na].O1CCN=C1>C(O)C>[CH2:16]([CH:17]1[O:14][CH:13]=[N:12][CH:11]1[S:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2])[CH3:15]

Komponenten

6

Edukt 4

HCID 527PropanalHCID 68157OxazolineHCID 5360545SodiumHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzene

Produkt 1

HCID 667581855-Ethyl-4-tosyl-2-oxazolineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred suspension of tosylmethylisocyanate (TosMIC, 3.90 g, 20 mmol) and propionaldehyde (1.5 mL 20.4 mmol) in 60 mL dry ethanol, finely powdered sodium cyamide (0.098 g, 2 mmol) was added. The reaction mixture became clear and white crystals of oxazoline began to precipitate in 15 min. The reaction was continuously stirred for an additional 30 min. The mixture was filtered and the crystals were washed with ether-hexane (1:1) before drying. Compound 15 was attained in 81% yield (4.1 g). The structure was confirmed by 1H NMR in CDCl3, LC-MS: [M+1]=254. Purity was >98%.

Aufarbeitung

  1. additionwas added
  2. customto precipitate in 15 min
  3. filtrationThe mixture was filtered
  4. washthe crystals were washed with ether-hexane (1:1)
  5. custombefore drying

Quellen und Nachweise

ORD-Eintrag
ord-97d179396b0740fb8856b9230ba3e5e7
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781442B2

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