3,4-dihydro-2H-pyran → 3-(5-chloro-1H-indol-3-yl)propan-1-ol

HRID 925306

반응식

HRID 925306 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>O.O1CCOCC1.C(OCC)(=O)C>[Cl:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH:16]=[C:15]2[CH2:14][CH2:13][CH2:12][OH:11]

참가 물질

6

반응물 2

HCID 80803,4-dihydro-2H-pyranHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)

생성물 1

HCID 199793473-(5-chloro-1H-indol-3-yl)propan-1-ol수율 64.4%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A mixture of (4-chlorophenyl)hydrazine hydrochloride (5.26 g; 28.50 mmol) and 3,4-dihydro-2H-pyran (2.63 mL; 28.50 mmol) in a mixture of water (9 mL) and dioxane (36 mL) was stirred at 100° C. for 48 hours. After cooling to room temperature the mixture was diluted with ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane) to afford 3.85 g (64%) of 3-(5-Chloro-1H-indol-3-yl)propan-1-ol as an oily residue.

후처리

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (eluent: 0 to 6% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-2bbcde54bbd045b79e1190ebcf378597
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284271B2

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