Potassium Carbonate → (3-Fluoro-6-nitro-2-vinylphenyl)-(1-methylallyl)amine

HRID 243212ノート

反応式

HRID 243212 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[C:3]=1[CH:12]=[CH2:13].[CH3:14][CH:15]([NH2:18])[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(O)C>[F:1][C:2]1[C:3]([CH:12]=[CH2:13])=[C:4]([NH:18][CH:15]([CH3:14])[CH:16]=[CH2:17])[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 15584178But-3-en-2-amine2 回HCID 681573311,3-Difluoro-4-nitro-2-vinylbenzene

生成物 1

HCID 68157256(3-Fluoro-6-nitro-2-vinylphenyl)-(1-methylallyl)amine収率 70%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1,3-difluoro-4-nitro-2-vinylbenzene (150 mg, 0.81 mmol) in DMF (3 mL) was added a mixture of 1-methylallylamine in ethanol (0.4 mL). Potassium carbonate (0.224 g, 1.62 mmol) was added and the mixture stirred at RT for 1 h. A further portion of 1-methylallylamine in ethanol (0.3 mL) was added and stirring was continued for 1 h, and then the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, eluant 2-6% EtOAc in cyclohexane) affording the title compound as a yellow oil (134 mg, 70%). 1H NMR (CDCl3, 300 MHz): 8.06 (1H, dd J=9.4, 5.7 Hz), 7.23 (1H, bs), 6.62 (1H, t, J=9.3 Hz), 6.48 (1H, dd, J=18.0, 11.6 Hz), 5.81-5.62 (2H, m), 5.64 (1H, dt, J=11.6, 1.3 Hz), 5.12-5.00 (2H, m), 4.38-4.25 (1H, m), 1.27 (3H, d, J=6.6 Hz)

後処理

  1. stirringstirring
  2. waitwas continued for 1 h
  3. customthe reaction mixture was partitioned between water and EtOAc
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic layers were washed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography (Si—PCC, eluant 2-6% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-f955077789a94d00889469c01a245820
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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