Methyl iodide → HCID 18994276、化合物

HRID 1647508ノート

反応式

HRID 1647508 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([OH:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH3:17]I>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([O:14][CH3:17])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19925593HCID 19925593、化合物

生成物 1

HCID 18994276HCID 18994276、化合物収率 77.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(3-aminophenyl)-4-hydroxytetrahydropyran (630 mg, 3.26 mmol), prepared as in step 3, in dry DMF (13 mL) was added sodium hydride (326 mg of a 60% oil dispersion). The reaction was stirred at ambient temperature for 1 hour and then methyl iodide (0.24 mL, 3.19 mmol) was added neat. The resulting solution was stirred at ambient temperature for 0.5 hour and quenched with saturated aqueous ammonium chloride. The biphasic solution was extracted with ethyl acetate. The organic layer was washed (1×, saturated aqueous ammonium chloride; 2×, brine), dried (MgSO4), and concentrated in vacuo to provide an oil. Chromatography on silica gel with 20% ethyl acetate/hexanes as the eluant provided 4-(3-aminophenyl)-4-methoxytetrahydropyran as a beige solid (510 mg, 76%). mp 99.0°-100.5° C. 1H NMR (300 MHz, CDCl3) δ7.17 (1H, t, J=9 Hz), 6.73- 6.82 (2H, m), 6.62 (1H, ddd, J=9, 2, 1 Hz), 3.85 (2H, td, J=10.5, 10.5, 2.5 Hz), 3.81 (2H, ddd, J=10.5, 9, 3 Hz), 2.99 (3H, s), 1.87-2.07 (4H, m). MS m/e 207 (M)+, 225 (M+NH4)+.

後処理

  1. stirringThe resulting solution was stirred at ambient temperature for 0.5 hour
  2. customquenched with saturated aqueous ammonium chloride
  3. extractionThe biphasic solution was extracted with ethyl acetate
  4. washThe organic layer was washed (1×, saturated aqueous ammonium chloride; 2×, brine)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto provide an oil

出典と根拠

ORDレコード
ord-d0fd7b8f09b14c5eb7839c6800ddba37
出典データセット
uspto-grants-1995_07
特許番号
US05432194

反応ノート

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