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

HRID 1698919

Reaction equation

HRID 1698919 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-b2d3ecb9c20f410bad57fd90f4b50329
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Linked notes

Loading…