Indole → 1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indole

HRID 244474

반응식

HRID 244474 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Cl[CH2:13][CH:14]1[CH2:18][O:17][C:16]([CH3:20])([CH3:19])[O:15]1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:19][C:16]1([CH3:20])[O:15][CH:14]([CH2:13][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH2:18][O:17]1

참가 물질

6

반응물 3

HCID 798IndoleHCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane2회HCID 24758Sodium hydride

생성물 1

HCID 594373201-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indole수율 28.5%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred room temperature solution of indole (5.9 g, 50 mmol) in THF (100 mL) was added sodium hydride (2.4 g of 60% in mineral oil, 60 mmol) in one portion. After 30 minutes, 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (10.6 mL, 75 mmol) was added followed by tetra-n-butylammonium iodide (1.9 g, 5 mmol) and the mixture was warmed at reflux. After 24 hours, LCMS showed about 50% conversion [MS m/z 232 (MH+)]. Additional 4-chloromethyl-2,2-dimethyl-1,3-dioxolane (11.4 mL) was added and the refluxing continued. After 18 hours, the mixture was cooled, diluted with THF (300 mL), filtered, and concentrated in vacuo to afford a brown oil. The residue was purified by column chromatography over silica gel eluting with 0-100% methylene chloride in hexanes and the product-rich fractions were collected to afford 3.3 g of 1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-1H-indole as a brownish oil.

후처리

  1. temperaturethe mixture was warmed
  2. temperatureat reflux
  3. waitAfter 24 hours
  4. waitAfter 18 hours
  5. temperaturethe mixture was cooled
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a brown oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-100% methylene chloride in hexanes
  10. customthe product-rich fractions were collected

출처 및 근거

ORD 기록
ord-c94e943c02ee4d41a5c763313e158079
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

연결된 노트

불러오는 중…