Sodium sulfate decahydrate → 2,3-dihydro-1H-indol-2-ylmethanol

HRID 55471

반응식

HRID 55471 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](OCC)=[O:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][OH:11]

참가 물질

5

반응물 3

HCID 62649Sodium sulfate decahydrateHCID 11949691Ethyl Indoline-2-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 27946642,3-dihydro-1H-indol-2-ylmethanol수율 95.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 5.12 g of ethyl indoline-2-carboxylate (prepared as described in Preparation 1) in 20 ml of anhydrous tetrahydrofuran was added dropwise, whilst ice-cooling, to a mixture of 1.20 g of lithium aluminum hydride and 80 ml of anhydrous tetrahydrofuran, and the resulting mixture was stirred at room temperature for 2 hours. After this, an excess of sodium sulfate decahydrate was added to the mixture, which was then stirred for 20 minutes. At the end of this time, insoluble materials were filtered off and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.81 g of the title compound having Rf=0.16 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

후처리

  1. stirringwas then stirred for 20 minutes
  2. filtrationAt the end of this time, insoluble materials were filtered off
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. customThe concentrate was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-aa94093ad1cc4760af2277f6f34bda10
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624935

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