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

HRID 2114327

반응식

HRID 2114327 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 590460Ethyl (2-oxo-1,3-benzoxazol-3(2H)-yl)acetate수율 103.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-6f9c4ab4879644dc9c95565cbb051b37
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432258B2

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