Water → 1-(2-Phenyl-benzoxazol-6-yl)butan-1-one

HRID 1619944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1619944
Br[C:2]1[CH:16]=[CH:15][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.C([Li])CCC.CON(C)[C:25](=[O:29])[CH2:26][CH2:27][CH3:28].O>C1COCC1.CCCCCC>[C:9]1([C:7]2[O:8][C:4]3[CH:3]=[C:2]([C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH:16]=[CH:15][C:5]=3[N:6]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 13704543N-Methoxy-N-methylbutyramideHCID 230259476-Bromo-2-phenylbenzo[d]oxazoleHCID 178418339Butyllithium

Produkt 1

HCID 674660111-(2-Phenyl-benzoxazol-6-yl)butan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

10.00 g (36.48 mmol) 6-bromo-2-phenyl-benzoxazole are dissolved in 180 ml THF and cooled to −70° C., and 35.00 ml (56.00 mmol) n-butyl lithium 1.6M in hexane are added dropwise. This solution cooled to −70° C. is added dropwise after 20 min to an equally cold −70° C. solution of 2.5 g (19.1 mmol) N-methoxy-N-methyl-butyramide and 20 ml THF. After 20 min further stirring the mixture is mixed with water and allowed to come up to RT. The reaction mixture is extracted with water and DCM, the org. phase is dried on magnesium sulphate and the solv. is eliminated by rotary evaporation i.V. The residue is separated through silica gel (eluant cyclohexane/EA).

Aufarbeitung

  1. temperatureThis solution cooled to −70° C.
  2. customto come up to RT
  3. extractionThe reaction mixture is extracted with water and DCM
  4. customphase is dried on magnesium sulphate
  5. customThe residue is separated through silica gel (eluant cyclohexane/EA)

Quellen und Nachweise

ORD-Eintrag
ord-992bd95e5141421d8d06238ce1f88e49
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08772323B2

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