Sodium hydride → 6-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 1468765

반응식

HRID 1468765 반응식
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:11](=[O:13])[O:10][CH2:9][C:8]=2[CH:14]=1.Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>CN(C)C=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[N:12]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:11](=[O:13])[O:10][CH2:9][C:8]=2[CH:14]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 259189636-Bromo-1,4-dihydro-2H-3,1-benzoxazin-2-one

생성물 1

HCID 679776606-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-2H-3,1-benzoxazin-2-one수율 85.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of sodium hydride (55 wt % in mineral oil, 1.36 g, 31.2 mmol) in N,N-dimethylformamide (37 ml) was added 6-bromo-1,4-dihydro-2H-3,1-benzoxazin-2-one (5.93 g, 26.0 mmol) in N,N-dimethylformamide (37 ml) at 0° C. The mixture was stirred at room temperature for one hour, then 2-(chloromethoxy)ethyltrimethylsilane (4.77 g, 28.6 mmol) was added at 0° C. The mixture was stirred at room temperature overnight. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with water (four times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=90/10 to 60/40) to afford 6-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydro-2H-3,1-benzoxazin-2-one as a pale yellow solid (7.96 g, 22.2 mmol, 85%).

후처리

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washThe organic layer was washed with water (four times)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=90/10 to 60/40)

출처 및 근거

ORD 기록
ord-0f78bfe11bc6498e94617a705081500e
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006232B2

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