Nitrogen → 1-(2-Hydroxymethyl-oxazol-4-yl)ethanone

HRID 2040039

Reaktionsgleichung

Reaktionsgleichung von HRID 2040039
N#N.C([SiH2][O:8][C:9](C)(C)[C:10]1[O:11][CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[N:14]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[OH:8][CH2:9][C:10]1[O:11][CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[N:14]=1

Komponenten

6

Edukt 3

HCID 947NitrogenHCID 2724141Tetrabutylammonium FluorideHCID 131730009HCID 131730009, Verbindung

Produkt 1

HCID 669287921-(2-Hydroxymethyl-oxazol-4-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-ethanone (192 mg, 0.75 mmol) in dry THF (5.0 mL) was treated at rt with TBAF (1.1 mL of a 1M solution in THF, 1.10 mmol). The reaction mixture was stirred at rt for 1.5 h. The mixture was then diluted with EA (10 mL), washed with brine (3×10 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (1:1 to 2:1 EA-Hept) gave the title compound as a pale yellow solid. TLC: rf (EA)=0.37. LC-MS-conditions 02: tR=0.34 min, [M+H]+=142.46.

Aufarbeitung

  1. washwashed with brine (3×10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by FC (1:1 to 2:1 EA-Hept)

Quellen und Nachweise

ORD-Eintrag
ord-87d3444119514695a4c4478f0a9e2086
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580831B2

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