Sodium hydride → 1-(2-Tetrahydropyranyloxyethyl)-4-benzyloxyindole

HRID 430774

反応式

HRID 430774 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28]Br.[NH4+].[Cl-]>CN(C=O)C>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:26][CH2:27][CH2:28][N:15]1[C:16]2[C:12](=[C:11]([O:10][CH2:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 884654-(phenylmethoxy)-1H-indole

生成物 1

HCID 538675441-(2-Tetrahydropyranyloxyethyl)-4-benzyloxyindole収率 92%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
0 °C

実験手順

Under argon atmosphere, sodium hydride (121 mg) in DMF (2 ml) was cooled to 0° C. and 4-benzyloxyindole (501 mg) in DMF (5 ml) was added thereto, followed by stirring the resulting solution at 0° C. for 5 minutes. To this solution, 2-tetrahydropyranyloxy-1-bromoethane (599 mg) in DMF (2 ml) was added and the solution was stirred at 0° C. for 30 minutes. The reaction mixture was added to saturated aqueous NH4Cl solution (30 ml) cooled at 0° C., and the resultant was extracted with ethyl acetate (3×20 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (722 mg, yield: 92%).

後処理

  1. stirringthe solution was stirred at 0° C. for 30 minutes
  2. temperaturecooled at 0° C.
  3. extractionthe resultant was extracted with ethyl acetate (3×20 ml)
  4. washThe obtained organic layers were washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removing solids
  7. filtrationby filtration
  8. customthe solvent was removed under reduced pressure
  9. customthe obtained crude product
  10. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-5fb0c8a871de4474adb5bd4d9c7d899f
出典データセット
uspto-grants-2001_11
特許番号
US06323235B1

関連ノート

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