Acetic Acid → 1-(4-Tert-butyl-2-nitrophenyl)-2,5-dimethylpyrrole

HRID 598434

反応式

HRID 598434 の反応式
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].CC(O)=O.[CH2:19]([CH2:23][C:24](=O)[CH3:25])[C:20]([CH3:22])=O>C1CCCCC1.C(Cl)Cl>[C:11]([C:9]1[CH:8]=[CH:7][C:5]([N:6]2[C:24]([CH3:25])=[CH:23][CH:19]=[C:20]2[CH3:22])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1)([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 80352,5-HexanedioneHCID 805734-tert-Butyl-2-nitroaniline

生成物 1

HCID 236145551-(4-Tert-butyl-2-nitrophenyl)-2,5-dimethylpyrrole収率 49%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8078Cyclohexane溶媒

反応条件

温度
120 °C

実験手順

To a stirring solution of 2-nitro-4-tert-butylaniline (0.5 g, 2.57 mmol) in cyclohexane (10 mL) was added AcOH (0.1 mL) and acetonylacetone (0.299 g, 2.63 mmol) via syringe. The reaction mixture was heated at 120° C. for 72 h with azeotropic removal of volatiles. The reaction mixture was cooled to room temp., diluted with CH2Cl2 (10 mL) and sequentially washed with a 1N HCl solution (15 mL), a 1N NaOH solution (15 mL) and a saturated NaCl solution (15 mL), dried (MgSO4) and concentrated under reduced pressure. The resulting orange-brown solids were purified via column chromatography (60 g SiO2; gradient from 6% EtOAc/94% hexane to 25% EtOAc/75% hexane) to give 1-(4-tert-butyl-2-nitrophenyl)-2,5-dimethylpyrrole as an orange-yellow solid (0.34 g, 49%)-TLC (15% EtOAc/85% hexane) Rf 0.67; 1H NMR (CDCl3) δ 1.34 (s, 9H), 1.89 (s, 6H), 5.84 (s, 2H), 7.19-7.24 (m, 1H), 7.62 (dd, 1H), 7.8 (d, J=2.4 Hz, 1H); CI-MS m/z 273 ((M+H)+, 50%).

後処理

  1. temperatureThe reaction mixture was cooled to room temp.
  2. washsequentially washed with a 1N HCl solution (15 mL)
  3. dry with materiala 1N NaOH solution (15 mL) and a saturated NaCl solution (15 mL), dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting orange-brown solids were purified via column chromatography (60 g SiO2; gradient from 6% EtOAc/94% hexane to 25% EtOAc/75% hexane)

出典と根拠

ORDレコード
ord-4b2d4a6b5adb48d8b4efa509b5f1b8ca
出典データセット
uspto-grants-2011_03
特許番号
US07897623B2

関連ノート

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