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Sodium hydride → methyl 2-oxo-1-(trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate

HRID 1176597
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HRID 1176597 반응식
[O:1]=[C:2]1[NH:8][C:7]2[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1.[H-].[Na+].[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:1]=[C:2]1[N:8]([CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])[C:7]2[C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=[CH:12][C:6]=2[CH2:5][CH2:4][CH2:3]1
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6

반응물 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 68497596Methyl 2-oxo-2,3,4,5-tetrahydro-1H-benz[b]azepine-9-carboxylate

생성물 1

HCID 68634682methyl 2-oxo-1-(trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

2.500 g of methyl 2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-9-carboxylate are dissolved under argon in 30 ml of N,N-dimethylformamide and the solution is cooled to 0° C. in an ice bath. 0.600 g of sodium hydride dispersion (60%) is added in portions and the reaction mixture is subsequently stirred at 0° C. over a further 1 hour. 0.502 ml of 2-(trimethylsilyl)ethoxymethyl chloride is added and the reaction mixture is subsequently stirred at room temperature over 11 hours. The reaction mixture is poured onto 150 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with 2×150 ml of tert-butyl methyl ether. The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a reddish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (1:1 EtOAc-heptane); Rt=5.02.

후처리

  1. stirringthe reaction mixture is subsequently stirred at room temperature over 11 hours
  2. extractionextracted with 2×150 ml of tert-butyl methyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-e92c9576896a4d9a86eda5158434931e
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842688B2

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