5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde

Base Information

• Chemical Name: 5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde
• CAS No.: 334474-30-5
• Molecular Formula: C₂₁H₂₄N₂OS
• Molecular Weight: 352.5

Synonyms:5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde

Chemical Property of 5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde

Chemical Property:

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Technology Process of 5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde

There total 1 articles about 5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

5-[1-(4,4-dimethyl-5-oxo-pyrrolidin-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester → 5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde (334474-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / Lawesson's reagent / toluene / 0.5 h / Heating

2: 71 percent / TFA

With Lawessons reagent; trifluoroacetic acid; In toluene;

DOI:10.1021/ol006983m

Reference yield: 73.0%

5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde (334474-30-5) + methylzinc iodide (18815-73-1) → Z-3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carbaldehyde (334474-33-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; toluene; at 75 ℃; for 0.5h;

DOI:10.1021/ol006983m

Reference yield:

5-[1-(4,4-dimethyl-5-methylsulfanyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde (334474-30-5) → Z-5-[1-(5-formyl-4,4-dimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde (334474-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / PdCl₂(PH₃P)2 / tetrahydrofuran; toluene / 0.5 h / 75 °C

2: 62 percent / SeO₂ / dioxane / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; selenium(IV) oxide; In tetrahydrofuran; 1,4-dioxane; toluene;

DOI:10.1021/ol006983m

Downstream raw materials:

Z-3,4-dimethyl-5-[1-(4,4,5-trimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-1H-pyrrole-2-carbaldehyde

Z-5-[1-(5-formyl-4,4-dimethyl-3,4-dihydropyrrol-2-ylidene)-phenyl-methyl]-3,4-dimethyl-1H-pyrrole-2-carbaldehyde

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