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

HRID 338905노트

반응식

HRID 338905 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1d93cae044df4edaafff656c6de19b39
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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