Triethylamine → (E)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-one

HRID 1527967Notes

Reaction equation

HRID 1527967 reaction equation
[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][N:13]=[N:12][CH:11]=1)[CH2:3]P(=O)(OC)OC.C(N(CC)CC)C.[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>C1COCC1>[Br:23][C:24]1[CH:31]=[CH:30][C:27](/[CH:28]=[CH:3]/[C:2]([C:10]2[CH:15]=[CH:14][N:13]=[N:12][CH:11]=2)=[O:1])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 707414-BromobenzaldehydeHCID 86684793Dimethyl 2-oxo-2-(pyridazin-4-yl)ethylphosphonate

Product 1

HCID 86684794(E)-3-(4-Bromophenyl)-1-(pyridazin-4-yl)prop-2-en-1-oneYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 2-oxo-2-(pyridazin-4-yl)ethylphosphonate (1.83 g, 7.95 mmol) in THF (18 mL) was added triethylamine (885 mg, 8.75 mmol) and 4-bromobenzaldehyde (1.49 g, 7.95 mmol) at 0° C. After 6 h the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. The residue was suspended in ethyl acetate and the title compound (824 mg, 36%) collected by filtration. Chromatography of the mother liquor (SiO2; ethyl acetate) produced a second crop of product (160 mg, 7%). Light yellow solid, MS: 288.9 [M+H]+.

Workup

  1. customAfter 6 h the reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. filtrationthe title compound (824 mg, 36%) collected by filtration

Sources & evidence

ORD record
ord-8f3ea2a39a7649aeb9e4cfa8bb7e7fe7
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

Loading…