Potassium Carbonate → Methyl 5-(2-methoxyethoxy)-2-nitrobenzoate

HRID 871317

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HRID 871317 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][O:24][CH3:25]>CN(C=O)C.O>[CH3:25][O:24][CH2:23][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

생성물 1

HCID 66639151Methyl 5-(2-methoxyethoxy)-2-nitrobenzoate수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

To methyl 5-hydroxy-2-nitrobenzoate (1.08 g, 5.5 mmol) in DMF (50 mL) was added potassium carbonate (1.52 g, 11 mmol) followed by 1-bromo-2-methoxyethane (1.55 mL, 16.4 mmol) and the mixture heated at 60° C. overnight. After cooling to room temperature, the reaction was diluted with H2O, extracted with EtOAc, and the organic layer washed with H2O and brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (12-100% EtOAc/hexanes) to give methyl 5-(2-methoxyethoxy)-2-nitrobenzoate (1.08 g, 4.2 mmol, 77%). 1H NMR (300 MHz, DMSO-d6) δ 8.13 (d, 1H), 7.31 (s, 1H), 7.29 (d, 1H), 4.29 (dd, 2H), 3.86 (s, 3H), 3.68 (dd, 2H), 3.31 (s, 3H); LC-MS (ESI) m/z 256 (M+H)+.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. washthe organic layer washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (12-100% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a09f2adf1d874fe385db8b04fa616e14
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969587B2

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