Hydrochloric Acid → 2,3-dihydro-1H-indol-2-ylmethanol

HRID 7421

반응식

HRID 7421 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[C:10](O)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.Cl>O1CCCC1>[OH:11][CH2:10][CH:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86074Indoline-2-carboxylic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 27946642,3-dihydro-1H-indol-2-ylmethanol수율 64.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of (RS)-indoline-2-carboxylic acid (8.16 g, 50 mmol) in tetrahydrofuran (50 ml) was added under ice-cooling lithium aluminum hydride (5.7 g, 150 mmol) and the mixture was stirred at 60° C. for 18 h. The reaction mixture was stirred under ice-cooling and ethanol and 1N hydrochloric acid were added. The precipitate was filtered off and the mother liquor was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was applied to silica gel column chromatography and eluted with ethyl acetate-hexane (1:4-1:1) to give the title compound (4.8 g, 64%).

후처리

  1. stirringThe reaction mixture was stirred under ice-
  2. temperaturecooling
  3. filtrationThe precipitate was filtered off
  4. washthe mother liquor was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washeluted with ethyl acetate-hexane (1:4-1:1)

출처 및 근거

ORD 기록
ord-44c45998a8b849329f98083d33b92282
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087597B1

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