Diethyl Ether → Methyl 2-(2-methylquinolin-8-yl)propanoate

HRID 338904ノート

反応式

HRID 338904 の反応式
[H-].[Na+].[CH3:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:9][CH:10]=2)[N:5]=1.IC.[CH3:21]COCC>CS(C)=O.C1COCC1.[Cl-].[Na+].O>[CH3:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([CH:14]([CH3:21])[C:15]([O:17][CH3:18])=[O:16])[CH:8]=[CH:9][CH:10]=2)[N:5]=1

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70984092Methyl 2-(2-methylquinolin-8-yl)acetate

生成物 1

HCID 70983048Methyl 2-(2-methylquinolin-8-yl)propanoate収率 100%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a mixture of NaH (0.58 g, 14.43 mmol) in DMSO (15 mL) at 20-35° C. was slowly added a solution of methyl 2-(2-methylquinolin-8-yl)acetate (1.35 g, 6.272 mmol) and iodomethane (1.08 ml, 17.25 mmol) in THF (5 mL). The reaction mixture was stirred at ambient temperature for 20 hours. Brine (20 mL) and ether (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give methyl 2-(2-methylquinolin-8-yl)propanoate (1.44 g, 100%) as an oil. The methyl 2-(2-methylquinolin-8-yl)propanoate (1.44 g, 6.28 mmol) was taken up in THF (10 mL) and 1 N lithium bis(trimethylsilyl)amide (12.56 mL, 12.56 mmol) in THF was added at 0° C. After addition, the reaction mixture was stirred at ambient temperature for 40 minutes. Iodomethane (0.78 mL, 12.56 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 18 hours. Water (10 mL) and ether (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (8:1 hexane/ethyl acetate) to give methyl 2-methyl-2-(2-methylquinolin-8-yl)propanoate (0.67 g, 43.9%) as an oil.

後処理

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-69e1d7b43c204ac68e4909a94babce1d
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…