Water → 3-Pyridazine-4-yl-acrylic acid methyl ester

HRID 705981Notes

Reaction equation

HRID 705981 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][N:2]=1.[CH3:9][O:10][C:11]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12].O>ClCCl>[CH3:9][O:10][C:11](=[O:12])[CH:13]=[CH:7][C:4]1[CH:5]=[CH:6][N:1]=[N:2][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 13011721Pyridazine-4-carbaldehyde

Product 1

HCID 677742593-Pyridazine-4-yl-acrylic acid methyl esterYield 113.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyridazine-4-carboxaldehyde (3.646 mmol, 1 eq) in dry dichloromethane (25 ml), (methoxycarbonylmethylene)triphenylphosphorane (5,550 mmol, 1.2 eq) was added portionwise. The reaction mixture was stirred at room temperature overnight. Reaction mixture was poured into water (200 ml) and extraction with DCM (3×100 ml) followed. Organic layers were combined, dried over phase separator cartridge to giving crude product which was purified on Biotage SP1 Snap Si 100; 40 ml/min in the gradient of MeOH in DCM: 0-10% in 30 CV. The appropriate fractions were combined and evaporated in vacuo to give the required product 3-pyridazine-4-yl-acrylic acid methyl ester (4.142 mmol, yield=89%, purity=96%). [M+H]+=165.11 1H NMR (300 MHz, CDCl3) δ/ppm 3.82 (s, 3H), 6.64-6.68 (m, 1H), 6.72 (s, 1H), 9.22 (dd, J=5.3, 1.0 Hz, 1H), 9.27 (s, 2H)

Workup

  1. customReaction mixture
  2. customdried over phase separator cartridge
  3. customto giving crude product which
  4. customwas purified on Biotage SP1 Snap Si 100
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-4fd1b2d9f2c34b6b907c539a20112a23
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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