Nitromethane → HCID 54315857, compound

HRID 1936620Notes

Reaction equation

HRID 1936620 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@H:9]1[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18]N(C)C(=N)N(C)C.[N+:26]([CH3:29])([O-:28])=[O:27]>>[C:1]([O:5][C:6]([C@H:8]1[CH2:10][C@H:9]1[CH:11]([CH2:18][CH2:29][N+:26]([O-:28])=[O:27])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 664601,1,3,3-Tetramethylguanidine2×HCID 54062723HCID 54062723, compound

Product 1

HCID 54315857HCID 54315857, compoundYield 85.9%

Procedure

To 60 ml of a nitromethane solution of 6.07 g (25.2 mmol) of ethyl 3-(cis-2-t-butoxycarbonylcyclopropyl)acrylate was added 3.48 ml (27.7 mmol) of tetramethylguanidine at room temperature, and the mixture was stirred for 6 hours. To the reaction mixture was further added 0.32 ml (2.52 mmol) of tetramethylguanidine, followed by stirring for 18 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15) to give 6.536 g (85.9%) of the title compound as a pale yellow oily substance.

Workup

  1. stirringby stirring for 18 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15)

Sources & evidence

ORD record
ord-0de922924a7a4dceb2da45e4154a29c6
Source dataset
uspto-grants-2002_05
Patent number
US06391889B1

Reaction notes

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