Methyl iodide → HCID 58554132、化合物

HRID 1630987ノート

反応式

HRID 1630987 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH3:17])=[C:8]([CH2:10][OH:11])[CH:9]=1.[CH3:18]I>CN(C=O)C>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH3:17])=[C:8]([CH2:10][O:11][CH3:18])[CH:9]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58554152HCID 58554152、化合物

生成物 1

HCID 58554132HCID 58554132、化合物収率 98.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of sodium hydride (2.84 g, 119 mmol) in anhydrous DMF (80 mL) was added a solution of [5-Bromo-2-(2-methylpyrrolidin-1-yl)phenyl]methanol (16 g, 59.2 mmol) in DMF (50 mL) drop wise at 0° C. After 30 minutes, methyl iodide (7.3 mL, 119 mmol) was added drop wise at 0° C. The reaction mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL), then diluted with water (200 mL) and extracted with EtOAc (150 ml). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (16.5 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 7.55 (1H, s), 7.29 (1H, m), 6.86 (1H, d), 4.45 (2H, s), 3.55 (1H, m), 3.41 (1H, m), 2.82 (1H, m), 2.12-2.51 (1H, m), 1.91 (1H, m) 1.81 (1H, m), 1.58 (1H, m), 0.99 (3H, d).

後処理

  1. customThe reaction mixture was quenched with a saturated aqueous solution of NH4Cl (20 mL)
  2. additiondiluted with water (200 mL)
  3. extractionextracted with EtOAc (150 ml)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b3daee04f2fa495da2451079463cbb8a
出典データセット
uspto-grants-2014_07
特許番号
US08791142B2

反応ノート

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