Potassium Carbonate → 5-(4-Bromophenyl)-4-ethyloxazole

HRID 1672580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672580
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:4][CH3:5])#[C-:2].[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]2[O:22][CH:2]=[N:1][C:3]=2[CH2:4][CH3:5])=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 204671891-Ethyl-1-tosylmethyl isocyanide

Produkt 1

HCID 666967705-(4-Bromophenyl)-4-ethyloxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(1-isocyanopropylsulfonyl)-4-methylbenzene (1.21 g, 5.40 mmol), 4-bromobenzaldehyde (1 g, 5 mmol), and K2CO3 (0.896 g, 6.49 mmol) in MeOH (27 mL) was heated at reflux overnight. The reaction was cooled to ambient temperature and the solvent was evaporated at reduced pressure. The residue was partitioned between water and EtOAc. The separated organic phase was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was dissolved in minimal toluene, loaded on silica gel, and eluted with 2 column volumes of hexane, then 10% to 50% EtOAc/hexanes. The result was 1.27 g (93%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 7.84 (s, 1H), 7.60-7.54 (m, 2H), 7.49-7.43 (m, 2H), 2.78 (q, J=7.5, 2H), 1.32 (t, J=7.6, 3H). MS (DCI+) m/z 252/254 (M+H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customthe solvent was evaporated at reduced pressure
  4. customThe residue was partitioned between water and EtOAc
  5. washThe separated organic phase was washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe crude product was dissolved in minimal toluene
  10. washeluted with 2 column volumes of hexane

Quellen und Nachweise

ORD-Eintrag
ord-98617a6edcb845ed8394373b6afe3cb2
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998993B2

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