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

HRID 1044556노트

반응식

HRID 1044556 반응식
[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]

참가 물질

5

반응물 3

HCID 6340Iodoethane2회HCID 24758Sodium hydride2회HCID 121909884,4-Dimethoxytetrahydro-2H-pyran-3-ol

생성물 1

HCID 579387433-Ethoxy-4,4-dimethoxytetrahydro-2H-pyran수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7bedb17697c24267b2c282eb01738855
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563582B2

반응 노트

불러오는 중…