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

HRID 55471

反応式

HRID 55471 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aa94093ad1cc4760af2277f6f34bda10
出典データセット
uspto-grants-1997_04
特許番号
US05624935

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