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

HRID 7421

反応式

HRID 7421 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](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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-44c45998a8b849329f98083d33b92282
出典データセット
uspto-grants-2006_08
特許番号
US07087597B1

関連ノート

読み込み中…