Acetic Acid → HCID 54140188, compound

HRID 1417536Notes

Reaction equation

HRID 1417536 reaction equation
[N+:1](=[CH2:3])=[N-:2].[Br:4][C:5]1[CH:6]=[C:7]([CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH3:15])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].C(O)(=O)C>CCOCC.C(OCC)(=O)C>[Br:4][C:5]1[CH:6]=[C:7]([CH:13]2[CH2:3][N:1]=[N:2][C:14]2([CH3:15])[N+:16]([O-:18])=[O:17])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 53843028HCID 53843028, compound

Product 1

HCID 54140188HCID 54140188, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ethereal solution of diazomethane (3.0 mL, 0.3M, 0.9 mmol) was added to 1-(3-bromo-4-methoxyphenyl)-2-nitropropene (250 mg, 0.92 mmol) dissolved in 2.5 mL of ether, and the solution was allowed to stand at room temperature for 28 h. Acetic acid (0.25 mL, 0.26 g, 4.4 mmol) was then added to the almost colorless solution, giving some gas evolution. After 15 min, the solution was diluted with 25 mL of ethyl acetate and washed with 10 mL of saturated aqueous sodium bicarbonate followed by 10 mL of saturated aqueous sodium chloride. The organic layer was dried (sodium sulfate), decanted, and evaporated to give 285 mg (99% yield) of a colorless oil which crystallized upon standing. 1H NMR (400 MHz, CDCl3): δ 7.17 (d, 1H, J=2 Hz), 6.89 (dd, 1H, J=8, 2 Hz), 6.84 (d, 1H, J=8 Hz), 5.21 (dd, 1H, J=18, 8 Hz), 4.97 (dd, 1H, J=18, 6 Hz), 3.90 (s, 3H), 3.77 (dd, 1H, J=8, 6 Hz), 1.60 (s, 3H).

Workup

  1. customgiving some gas evolution
  2. waitAfter 15 min
  3. washwashed with 10 mL of saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. customdecanted
  6. customevaporated

Sources & evidence

ORD record
ord-d78ff89ea8244bec8f13e32660faaa41
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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