Dimethyl Sulfate → Methyl 5-t-butyl-1-methyl-3-nitropyrrole-2-carboxylate

HRID 1698919

반응식

HRID 1698919 반응식
[C:1]([C:5]1[NH:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(OC)(O[CH3:21])(=O)=O.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)Cl>[C:1]([C:5]1[N:9]([CH3:21])[C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 18322358methyl 5-tert-butyl-3-nitro-1H-pyrrole-2-carboxylate

생성물 1

HCID 18322374Methyl 5-t-butyl-1-methyl-3-nitropyrrole-2-carboxylate

시약·촉매·용매 2

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromide촉매HCID 6344Dichloromethane용매

실험 절차

To a cold (0-10° C.) solution of methyl 5-tert-butyl-3-nitropyrrole-2-carboxylate (0.100 g, 0.44 mmol), benzyltributylammonium bromide (0.16 mg, 0.44 mmol, 1 equiv), and dimethyl sulfate (46 μL, 0.49 mmol, 1.1 equiv) in CH2Cl2 (1 mL) was added a 50% NaOH solution (0.21 g, 2.65 mmol, 6 equiv). After 5 min, the cooling bath was removed and the mixture was stirred at room temp. for 4 h. The reaction mixture was diluted with CH2Cl2, washed with water and a 10% NH4OAc solution (2x), dried (Na2SO4), and concentrated under reduced pressure to give a bright yellow oil. The oil was purified by flash chromatography (70% CH2Cl2/hexane) to give methyl 5-tert-butyl-1-methyl-3-nitropyrrole-2-carboxylate as a pale yellow oil which solidifies upon standing (0.061 g, 62%): 1H NMR (CDCl3) δ1.38 (s, 9H)., 3.80 (s, 3H), 3.92 (s, 3H), 6.47 (s, 1H).

후처리

  1. customthe cooling bath was removed
  2. additionThe reaction mixture was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materiala 10% NH4OAc solution (2x), dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a bright yellow oil
  7. customThe oil was purified by flash chromatography (70% CH2Cl2/hexane)

출처 및 근거

ORD 기록
ord-b2d3ecb9c20f410bad57fd90f4b50329
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06344476B1

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