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

HRID 430774

반응식

HRID 430774 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 538675441-(2-Tetrahydropyranyloxyethyl)-4-benzyloxyindole수율 92%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5fb0c8a871de4474adb5bd4d9c7d899f
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323235B1

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