Ethyl Acetate → 2-{2-Bromomethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl ester

HRID 1181141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181141
[CH2:1]([O:3][C:4](=[O:32])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30]O)([CH3:7])[CH3:6])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:53].CCOC(C)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:32])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][Br:53])([CH3:7])[CH3:6])[CH3:2]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 235900112-{2-Hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl ester

Produkt 1

HCID 235900072-{2-Bromomethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}-2-methylpropionic acid ethyl esterAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 100 mL round bottomed flask was charged with 2-{2-hydroxymethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenoxy}-2-methyl-propionic acid ethyl ester (1.0 g, 2.25 mmol), dissolved in anhydrous THF (75 mL), and then of triphenylphosphine (1.18 g, 4.50 mmol) and CBr4 (1.49 g, 4.50 mmol). The mixture was stirred at ambient temperature under a nitrogen atmosphere for 1 h and was poured into EtOAc (135 mL). The organic layer was washed with brine (50 mL), dried (Na2SO4), and concentrated. The crude product was purified using radial chromatography (EtOAc:hexanes 15:85) to give a the title compound as a colorless oil (0.95 g, 76%).

Aufarbeitung

  1. washThe organic layer was washed with brine (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-a5289515750c4bad9d18802475616a79
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282501B2

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