4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: 4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester
• CAS No.: 75116-24-4
• Molecular Formula: C₁₈H₁₈Cl₃NO₄
• Molecular Weight: 418.704

Synonyms:4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester

Chemical Property of 4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester

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Technology Process of 4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester

There total 1 articles about 4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester 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:

benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate (20303-31-5) → 4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester (75116-24-4)

Guidance literature:

With thionyl chloride; In tetrachloromethane; Ambient temperature;

DOI:10.1055/s-1980-29071

Reference yield:

4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester (75116-24-4) → benzyl 3-<2-(methoxycarbonyl)ethyl>-4-methylpyrrole-5-carboxylate (31896-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₃CO₂Na*3H₂O / dioxane; H₂O / 1) 70 deg C, 1.5 h, 2) rt, overnight

2: 95 percent / NaHCO₃, I₂, KI / methanol; H₂O / 1 h / 60 - 65 °C

3: 92 percent / CH₃CO₂Na, H₂ / PtO₂ / ethanol / 24 h / 1551.4 Torr / Ambient temperature

With hydrogen; iodine; sodium acetate; sodium hydrogencarbonate; potassium iodide; platinum(IV) oxide; In 1,4-dioxane; methanol; ethanol; water;

DOI:10.1016/S0040-4020(01)85734-3

Reference yield:

4-(2-Methoxycarbonyl-ethyl)-3-methyl-5-trichloromethyl-1H-pyrrole-2-carboxylic acid benzyl ester (75116-24-4) → Benzyl 6-Hydroxy-3-methylcyclopentapyrrole-2-carboxylate (145696-30-6)

Guidance literature:

Multi-step reaction with 6 steps

1: CH₃CO₂Na*3H₂O / dioxane; H₂O / 1) 70 deg C, 1.5 h, 2) rt, overnight

2: 95 percent / NaHCO₃, I₂, KI / methanol; H₂O / 1 h / 60 - 65 °C

3: 92 percent / CH₃CO₂Na, H₂ / PtO₂ / ethanol / 24 h / 1551.4 Torr / Ambient temperature

4: 91 percent / aq. HCl / acetone / 3 h / Heating

5: 1a) KOH, 1b) oxalyl chloride / 2) SnCl₄ / 1a) CH₃OH, 1b) toluene, rt, 3 h, 2) rt, 1 h

6: 82 percent / NaBH₄ / 1) ethanol, rt, 10 min, 2) water, heating

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; oxalyl dichloride; hydrogen; iodine; sodium acetate; sodium hydrogencarbonate; potassium iodide; platinum(IV) oxide; tin(IV) chloride; In 1,4-dioxane; methanol; ethanol; water; acetone;

DOI:10.1016/S0040-4020(01)85734-3

upstream raw materials:

benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate

Downstream raw materials:

5-benzyloxycarbonyl-3-(2-methoxycarbonylethyl)-4-methylpyrrole-2-carboxylic acid

tert-Butyl 5-(Benzyloxycarbonyl)-3-(2'-(methoxycarbonyl)ethyl)-4-methylpyrrole-2-carboxylate

benzyl 3-<2-(methoxycarbonyl)ethyl>-4-methylpyrrole-5-carboxylate

Benzyl 5-Iodo-4-(2-methoxycarbonylethyl)-3-methylpyrrole-2-carboxylate

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