Methyl iodide → Dimethyl 2-methyl-2-(4-nitrophenyl)malonate

HRID 1842969노트

반응식

HRID 1842969 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:19]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[CH3:19][C:10]([C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2764303Dimethyl 2-(4-nitrophenyl)malonate

생성물 1

HCID 1485451Dimethyl 2-methyl-2-(4-nitrophenyl)malonate수율 66.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of dimethyl 2-(4-nitrophenyl)malonate (10 g, 39.52 mmol, 1.0 eq) and K2CO3 (10.9 g 79.05 mmol 2.0 eq) in DMF (40 mL), was added methyl iodide (4.94 mL, 79.05 mmol 2.0 eq) at 0° C. and the mixture stirred at RT for 18 h. K2CO3 was filtered out and the filtrate concentrated under vacuum. The residue was diluted with water (80 mL) and extracted with EtOAc (2×80 mL). The organic layer was separated washed with brine solution, dried over anhydrous Na2SO4 and the solvent evaporated to get dimethyl 2-methyl-2-(4-nitrophenyl)malonate (7 g, 66%; TLC system: EtOAc/PE (3:7), Rf: 0.5.)

후처리

  1. filtrationK2CO3 was filtered out
  2. concentrationthe filtrate concentrated under vacuum
  3. additionThe residue was diluted with water (80 mL)
  4. extractionextracted with EtOAc (2×80 mL)
  5. customThe organic layer was separated
  6. washwashed with brine solution
  7. dry with materialdried over anhydrous Na2SO4
  8. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-0ac5f0688225410bafab0b1d96e24146
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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