2(3H)-Benzoxazolone → Ethyl (2-oxo-1,3-benzoxazol-3(2H)-yl)acetate

HRID 2354321

Reaktionsgleichung

Reaktionsgleichung von HRID 2354321
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[H-].[Na+].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C>[O:10]=[C:2]1[N:3]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1]1

Komponenten

5

Edukt 3

HCID 60432(3H)-BenzoxazoloneHCID 7748Ethyl bromoacetateHCID 24758Sodium hydride

Produkt 1

HCID 590460Ethyl (2-oxo-1,3-benzoxazol-3(2H)-yl)acetateAusbeute 103,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1,3-benzoxazol-2(3H)-one (676 mg, 5.0 mmol) in (5 mL) was added to a suspension of NaH (220 mg, 5.5 mmol) in DMF (5 mL) at room temperature, and the resulting solution was stirred for 1 h. Ethyl bromoacetate (0.55 mL, 5.0 mmol) was added to the reaction mixture, and stirring was continued for 2 h. The reaction was quenched with water (10 mL) and extracted with EtOAc (2×20 mL). The organic extracts were combined and washed with water, brine, and dried (Na2SO4). The solvent was removed under reduced pressure to give the title compound (1.14 g, >100%) as a brown solid. MS (ES) m/e 222 [M+H]+.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 2 h
  3. customThe reaction was quenched with water (10 mL)
  4. extractionextracted with EtOAc (2×20 mL)
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-93090c895ceb407c8ebfea98132bc389
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749998B2

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