Methyl iodide → 4-Methoxy-1-(2-methoxyethyl)-2-nitrobenzene

HRID 1914692

反応式

HRID 1914692 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[H-].[Na+].I[CH3:18]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][CH3:18])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 198355352-(4-Methoxy-2-nitrophenyl)ethan-1-ol

生成物 1

HCID 593530064-Methoxy-1-(2-methoxyethyl)-2-nitrobenzene収率 63.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-(4-methoxy-2-nitrophenyl)ethanol (1 g; 5.07 mmol; 1 eq) in THF (50 mL) is added sodium hydride (406 mg; 10.14 mmol; 2 eq) at 0° C. and the reaction mixture is stirred at 0° C. for 10 min before adding iodomethane (0.63 mL; 10.14 mmol; 2 eq). The reaction mixture is stirred overnight. It is quenched by addition of water. The product is extracted with EtOAc and the organic phase is dried over MgSO4. The solvent is evaporated under reduced pressure and the residue is purified by flash chromatography using a mixture of petrol ether and EtOAc (70/30) as eluent. The solvents are evaporated to afford 680 mg (63%) of the title compound as a yellow solid. 1H NMR (DMSO-d6) δ 7.35 (d, J=3.0 Hz, 1H), 7.21 (d, J=9.0 Hz, 1H), 6.98 (dd, J=9.0, 3.0 Hz, 1H), 3.76 (s, 3H), 3.54 (t, J=9.0 Hz, 2H), 3.24 (s, 314), 3.01 (t, J=9.0 Hz, 2H), HPLC (max plot) 94%; Rt 4.18 min.

後処理

  1. stirringThe reaction mixture is stirred overnight
  2. customIt is quenched by addition of water
  3. extractionThe product is extracted with EtOAc
  4. dry with materialthe organic phase is dried over MgSO4
  5. customThe solvent is evaporated under reduced pressure
  6. customthe residue is purified by flash chromatography
  7. additiona mixture of petrol ether and EtOAc (70/30) as eluent
  8. customThe solvents are evaporated

出典と根拠

ORDレコード
ord-a9506a830cbe4985be59d28e7bf0d98c
出典データセット
uspto-grants-2013_12
特許番号
US08614215B2

関連ノート

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