Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate → Dimethyl 5-(2-nitrovinyl)isophthalate

HRID 587937Notes

Reaction equation

HRID 587937 reaction equation
O[CH:2]([C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])[CH2:3][N+:4]([O-:6])=[O:5]>C(Cl)Cl.C(OC(=O)C)(=O)C.CN(C)C1C=CN=CC=1>[N+:4]([CH:3]=[CH:2][C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])([O-:6])=[O:5]

Participants

5

Reactant 1

HCID 68474723Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate

Product 1

HCID 68478188Dimethyl 5-(2-nitrovinyl)isophthalate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 2.29 g (8.09 mmol) of dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate in 50 mL of DCM and 10 mL of acetic anhydride at 22° C. was added 100 mg of 4-dimethylaminopyridine. The solution was stirred at 22° C. for 1.5 h, evaporated and then coevaporated with xylenes (the material darkened slightly). The residue was partitioned between 100 mL of DCM and 50 mL of 1 N HCl. The organic layer was washed with water (50 mL), satd NaHCO3, dried (Na2SO4) and evaporated. The resulting residue was purified by flash chromatography on silica gel eluting with DCM to give dimethyl 5-(2-nitrovinyl)isophthalate as a light yellow solid.

Workup

  1. customevaporated
  2. customThe residue was partitioned between 100 mL of DCM and 50 mL of 1 N HCl
  3. washThe organic layer was washed with water (50 mL), satd NaHCO3
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe resulting residue was purified by flash chromatography on silica gel eluting with DCM

Sources & evidence

ORD record
ord-779c57fb7faa4cbc952e9c7e62459a33
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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