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

HRID 1842969ノート

反応式

HRID 1842969 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.)

後処理

  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

出典と根拠

ORDレコード
ord-0ac5f0688225410bafab0b1d96e24146
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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