Water → 3-Pyridinepropanol

HRID 22487

反応式

HRID 22487 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9](/[CH:13]=[CH:14]/[C:15](OC)=[O:16])[CH:8]=1.O.[OH-].[Na+]>C(OCC)C>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][OH:16])[CH:8]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 53576873-Pyridineacrylic acid, methyl esterHCID 21226445Aluminium lithium hydride

生成物 1

HCID 178613-Pyridinepropanol

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To an ice cold mixture of lithium aluminium hydride (28 mg, 0.74 mmol) in dry diethyl ether (20 ml) was added dropwise methyl E-3-(3-pyridyl)acrylate (100 mg, 0.61 mmol) under argon. The resulting mixture was allowed to warm up to room temperature and stirred for 12 h. Water (0.1 ml), 15% aqueous sodium hydroxide (0.1 ml) and water (0.3 ml) were added sequentially over 0.5 h and the mixture allowed to stir for 1 h. The resulting suspension was filtered and the filtrate concentrated under reduced pressure. Flash chromatography (flash silica gel; 10% methanol in ethyl acetate) gave 3-(3-pyridyl)-1-propanol, which was discarded, and E-3-(3-pyridyl)-1-prop-2-enol (55 mg, 67%) as a colourless oil.

後処理

  1. stirringto stir for 1 h
  2. filtrationThe resulting suspension was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-542be1b40c894345ad8add272bc4e44e
出典データセット
uspto-grants-1995_06
特許番号
US05428168

関連ノート

読み込み中…