Iodoethane → 3-Ethoxy-4,4-dimethoxytetrahydro-2H-pyran

HRID 1044556ノート

反応式

HRID 1044556 の反応式
[CH3:1][O:2][C:3]1([O:10][CH3:11])[CH2:8][CH2:7][O:6][CH2:5][CH:4]1[OH:9].[H-].[Na+].I[CH2:15][CH3:16]>C1COCC1>[CH2:15]([O:9][CH:4]1[C:3]([O:10][CH3:11])([O:2][CH3:1])[CH2:8][CH2:7][O:6][CH2:5]1)[CH3:16]

参加物

5

反応物 3

HCID 6340Iodoethane2 回HCID 24758Sodium hydride2 回HCID 121909884,4-Dimethoxytetrahydro-2H-pyran-3-ol

生成物 1

HCID 579387433-Ethoxy-4,4-dimethoxytetrahydro-2H-pyran収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4,4-dimethoxytetrahydro-2H-pyran-3-ol (2.0 g, 12 mmol) in THF (20 mL) cooled in an ice bath was slowly added sodium hydride (0.60 g, 15 mmol) and the resulting slurry was stirred for 1 h. Iodoethane (1.5 mL, 19 mmol) was added and the mixture was stirred at room temperature overnight. More sodium hydride (0.6 g) and iodoethane (3 mL) were added and stirring was continued another overnight. The reaction was quenched with water. The resulting solution was extracted with EtOAc twice and ether twice. The combined extracts were dried, concentrated and purified on silica gel (20% EtOAc/hexanes) to give 2.1 g (90%) of desired product. 1H NMR (CDCl3) δ 3.32-4.00 (7H, m), 3.30 (3H, s), 3.20 (3H, s), 2.05-1.70 (2H, m), 1.25-1.22 (3H, m).

後処理

  1. stirringthe mixture was stirred at room temperature overnight
  2. stirringstirring
  3. waitwas continued another overnight
  4. customThe reaction was quenched with water
  5. extractionThe resulting solution was extracted with EtOAc twice
  6. customThe combined extracts were dried
  7. concentrationconcentrated
  8. custompurified on silica gel (20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-7bedb17697c24267b2c282eb01738855
出典データセット
uspto-grants-2013_10
特許番号
US08563582B2

反応ノート

読み込み中…