Water → Methyl 2-methyl-2-(2-methylquinolin-8-yl)propanoate

HRID 338905ノート

反応式

HRID 338905 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:18][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC.O>C1COCC1.CCOCC>[CH3:17][C:12]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2)([CH3:18])[C:13]([O:15][CH3:16])=[O:14]

参加物

7

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 70983048Methyl 2-(2-methylquinolin-8-yl)propanoate

生成物 1

HCID 70984004Methyl 2-methyl-2-(2-methylquinolin-8-yl)propanoate収率 43.9%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

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. additionAfter addition
  2. stirringthe reaction mixture was stirred at ambient temperature for 18 hours
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel (8:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-1d93cae044df4edaafff656c6de19b39
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

反応ノート

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