Potassium Carbonate → 4-Ethyl-5-[4-(trifluoromethyl)phenyl]oxazole

HRID 1672572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672572
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[N+:13]([CH:15](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:16][CH3:17])#[C-:14].C([O-])([O-])=O.[K+].[K+]>CO>[CH2:16]([C:15]1[N:13]=[CH:14][O:8][C:7]=1[C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:11])([F:12])[F:1])=[CH:4][CH:5]=1)[CH3:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 679964-(Trifluoromethyl)benzaldehydeHCID 204671891-Ethyl-1-tosylmethyl isocyanide

Produkt 1

HCID 666965954-Ethyl-5-[4-(trifluoromethyl)phenyl]oxazoleAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(trifluoromethyl)benzaldehyde (3.60 mL, 27.0 mmol), 1-(1-isocyanopropylsulfonyl)-4-methylbenzene (6.02 g, 27.0 mmol), and K2CO3 (4.47 g, 32.4 mmol) in MeOH (100 mL) was heated to reflux. After 1.5 hr the reaction mixture was cooled to ambient temperature, and the volatiles evaporated at reduced pressure. The residue was partitioned between Et2O (100 mL) and H2O (100 mL). The separated aqueous phase was extracted with Et2O. The combined organic extract was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. Chromatography on silica gel (Analogix® Intelliflash 280™; SF40-150 g column; 10% to 30% EtOAc/hexanes eluant, 30 min) afforded 5.75 g (88%) of the title compound as a pale yellow oil. 1H NMR (300 MHz, DMSO-d6) δ 8.44 (s, 1H), 7.90-7.78 (m, 4H), 2.79 (q, J=7.5, 2H), 1.23 (t, J=7.5, 3H). MS (DCI+) m/z 242 (M+H).

Aufarbeitung

  1. temperaturewas heated to reflux
  2. customthe volatiles evaporated at reduced pressure
  3. customThe residue was partitioned between Et2O (100 mL) and H2O (100 mL)
  4. extractionThe separated aqueous phase was extracted with Et2O
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d05a13115b46489fa8f87cfcdcb3824e
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998993B2

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