t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

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Chemical Name:t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate
CAS No.:242127-03-3
Molecular Formula:C₃₁H₃₈N₂O₅S
Molecular Weight:550.719
Hs Code.:

Synonyms:t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

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Chemical Property of t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

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Technology Process of t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

There total 8 articles about t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate 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: 90.0%

: 208753-55-3
t-butyl 3-(3-allyloxy-3-oxopropyl)-5-formyl-4-methyl-1H-pyrrole-2-carboxylate

: 242127-00-0
3-methyl-4-[2-(p-tolylthio)ethyl]-5-tosyl-1,5-dihydro-2H-pyrrol-2-one

: 242127-03-3
t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

Guidance literature:: t-butyl 3-(3-allyloxy-3-oxopropyl)-5-formyl-4-methyl-1H-pyrrole-2-carboxylate; 3-methyl-4-[2-(p-tolylthio)ethyl]-5-tosyl-1,5-dihydro-2H-pyrrol-2-one; With tributylphosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20 ℃; for 8h;

With iodine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 4h;
DOI:10.1246/cl.2009.602

Reference yield: 60.0%

: 208753-55-3
t-butyl 3-(3-allyloxy-3-oxopropyl)-5-formyl-4-methyl-1H-pyrrole-2-carboxylate

: 242127-00-0
3-methyl-4-[2-(p-tolylthio)ethyl]-5-tosyl-1,5-dihydro-2H-pyrrol-2-one

: t-butyl 3-(3-allyloxy-3-oxopropyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

: 242127-03-3
t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

Guidance literature:: With tributylphosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; Title compound not separated from byproducts;
DOI:10.1246/bcsj.79.1561

Reference yield:

: 120483-06-9
3-p-Tolylsulfanyl-propionaldehyde

: 242127-03-3
t-butyl 3-(2-allyloxycarbonylethyl)-4-methyl-5-({4-methyl-5-oxo-3-[2-(p-tolylthio)ethyl]-1H-pyrrol-2(5H)-ylidene}methyl)-1H-pyrrole-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / KOH / methanol

2: DMAP / tetrahydrofuran / 0.17 h / Ambient temperature

3: 96 percent / DBU / acetonitrile / 1.) -40 deg C to r.t., 2.) r.t., overnight

4: 98 percent / PhMe₃N(+)Br₃(-) / CH₂Cl₂ / 0.17 h / 0 °C

5: 63 percent / TFA, H₂O / 4 h / Ambient temperature

6: 1.) DBU, PBu₃, 2.) I₂ / 1.) THF, r.t., 21 h, 2.) CH₂Cl₂, r.t., 2 d

With dmap; potassium hydroxide; tributylphosphine; water; iodine; phenyltrimethylammonium tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1055/s-1999-3105