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

HRID 244474

反応式

HRID 244474 の反応式
[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

参加物

6

反応物 3

HCID 798IndoleHCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane2 回HCID 24758Sodium hydride

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c94e943c02ee4d41a5c763313e158079
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

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