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

HRID 338904노트

반응식

HRID 338904 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매HCID 57417360Sodium chloride; water용매

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

출처 및 근거

ORD 기록
ord-69e1d7b43c204ac68e4909a94babce1d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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