Sodium sulfate decahydrate → 2-(2-Methylquinolin-7-yl)propane-1,3-diol

HRID 339076ノート

反応式

HRID 339076 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([C:24](OCC)=[O:25])[C:19](OCC)=[O:20])=[CH:13][CH:14]=2)[N:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOCC>[CH3:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([CH2:24][OH:25])[CH2:19][OH:20])=[CH:13][CH:14]=2)[N:9]=1

参加物

6

反応物 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 70984111Diethyl 2-(2-methylquinolin-7-yl)malonate

生成物 1

HCID 709837452-(2-Methylquinolin-7-yl)propane-1,3-diol収率 41%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1.0 N LAH (15.3 mL, 15.3 mmol) in THF was added diethyl 2-(2-methylquinolin-7-yl)malonate (1.15 g, 3.82 mmol) in Ether (30 mL) slowly at 0° C. The reaction mixture was stirred at 0° C. for 2 hours. Sodium sulfate decahydrate (2.0 g) was added and stirred at ambient temperature for 30 minutes. The solid was removed by filtration and washed with ethyl acetate (50 mL). The filtrate was concentrated and the residue obtained was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 40M column, 0-70% CH3CN/water gradient; 30 CV) to give 2-(2-methylquinolin-7-yl)propane-1,3-diol (0.34 g, 1.56 mmol, 41.0% yield) as a solid.

後処理

  1. stirringstirred at ambient temperature for 30 minutes
  2. customThe solid was removed by filtration
  3. washwashed with ethyl acetate (50 mL)
  4. concentrationThe filtrate was concentrated
  5. customthe residue obtained
  6. customwas purified by C-18 reverse phase flash chromatography (Biotage SP4 unit

出典と根拠

ORDレコード
ord-c17a68cf22244f08804d5565569d321b
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

読み込み中…