Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 69527169, compound

HRID 860514Notes

Reaction equation

HRID 860514 reaction equation
[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]([CH2:21][O:22][CH3:23])[C:10]([CH:19]=O)=[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)[C:6]2=[CH:5][CH:4]=1)[CH3:2].[CH2:24]([O:26][C:27](=[O:48])[CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:25]>C1COCC1>[CH2:1]([C:3]1[N:7]2[N:8]=[C:9]([CH2:21][O:22][CH3:23])[C:10](/[CH:19]=[CH:28]/[C:27]([O:26][CH2:24][CH3:25])=[O:48])=[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)[C:6]2=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86597481HCID 86597481, compound

Product 1

HCID 69527169HCID 69527169, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-ethyl-2-(methoxymethyl)-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazine-3-carbaldehyde (48 mg) and ethyl(triphenylphosphoranylidene)acetate (56.8 mg) in THF (3 mL) was stirred at ambient temperature for 2 hours. After evaporation of solvent, the residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (5:1-2:1) to give ethyl(2E)-3-[7-ethyl-2-(methoxymethyl)-4-(5-methyl-3-pyridinyl)pyrrolo[1,2-b]pyridazin-3-yl]acrylate as a yellow powder (30 mg).

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with a mixture of hexane and AcOEt (5:1-2:1)

Sources & evidence

ORD record
ord-58a955db9a3140fe9e856de39800db41
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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