1-Nitroethylene → HCID 54136732, compound

HRID 361298Notes

Reaction equation

HRID 361298 reaction equation
[CH3:1][N+:2]([O-:16])=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([O:12][CH3:13])[C:5]=1[O:14][CH3:15].[N+:17]([CH:20]=[CH2:21])([O-:19])=[O:18]>C1(C)C=CC=CC=1>[CH3:15][O:14][C:5]1[C:6]([O:12][CH3:13])=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[CH:3]1[CH:20]([N+:17]([O-:19])=[O:18])[CH2:21][O:16][N:2]1[CH3:1]

Participants

4

Reactant 2

HCID 771971-NitroethyleneHCID 85728081HCID 85728081, compound

Product 1

HCID 54136732HCID 54136732, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 5.88 g (26.1 mmol) portion of N-methyl-C-(2,3,4-trimethoxyphenyl)nitrone was added to 50 mL of 0.76 molar (38 mmol) nitroethylene in toluene. The mixture was heated at reflux for 2 h. The solvent was removed in vacuo to leave a brown tar which was purified by flash chromatography on a column of 50 g of silica gel eluted successively with 100 mL portions of 0, 10, 20, 30, 40 and 50% ether in hexanes to yield 4.53 g of an orange oil. This material was crystallized from 20 mL of ice-cold 1:1 ether:hexanes to give 3.16 g of 2-methyl-4-nitro-3-(2,3,4-trimethoxyphenyl)-isoxazolidine (Example 38) as a low melting solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customThe solvent was removed in vacuo
  4. customto leave a brown tar which
  5. customwas purified by flash chromatography on a column of 50 g of silica gel
  6. washeluted successively with 100 mL portions of 0, 10, 20, 30, 40 and 50% ether in hexanes

Sources & evidence

ORD record
ord-1f3f9246f1f04c359ad98ad7487406d7
Source dataset
uspto-grants-1999_02
Patent number
US05866513

Reaction notes

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