3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester
CAS No.:242127-10-2
Molecular Formula:C₃₁H₃₈N₂O₅S
Molecular Weight:550.719
Hs Code.:

3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-<i>p</i>-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1<i>H</i>-pyrrole-2-carboxylic acid <i>tert</i>-butyl ester

Synonyms:3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

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Chemical Property of 3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

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Technology Process of 3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

There total 5 articles about 3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl 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: 79.0%

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

: 242127-09-9
1,5-dihydro-4-methyl-3-[2-(tolylthio)ethyl]-5-tosyl-2H-pyrrol-2-one

: 242127-10-2
3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Guidance literature:: t-butyl 3-(3-allyloxy-3-oxopropyl)-5-formyl-4-methyl-1H-pyrrole-2-carboxylate; 1,5-dihydro-4-methyl-3-[2-(tolylthio)ethyl]-5-tosyl-2H-pyrrol-2-one; With tributylphosphine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20 ℃; for 6h;

With iodine; In dichloromethane; at 20 ℃;
DOI:10.1246/cl.2001.590

Reference yield:

: 242127-08-8
2-bromo-4-methyl-5-(toluene-4-sulfonyl)-3-(2-p-tolylsulfanyl-ethyl)-1H-pyrrole

: 242127-10-2
3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: DMSO / trifluoroacetic acid / 2 h / 20 °C

1.2: 81 percent / I₂; Zn / 2 h / 20 °C

2.1: nBu₃P; DBU / tetrahydrofuran / 6 h / 0 - 20 °C

2.2: 79 percent / I₂ / CH₂Cl₂ / 20 °C

With tributylphosphine; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; trifluoroacetic acid;
DOI:10.1246/cl.2001.590

Reference yield:

: 242127-07-7
3-methyl-2-(toluene-4-sulfonyl)-4-(2-p-tolylsulfanyl-ethyl)-1H-pyrrole

: 242127-10-2
3-(2-allyloxycarbonyl-ethyl)-4-methyl-5-[3-methyl-5-oxo-4-(2-p-tolylsulfanyl-ethyl)-1,5-dihydro-pyrrol-2-ylidenemethyl]-1H-pyrrole-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: PhMe₃N(+)Br₃(-) / CH₂Cl₂ / 0.17 h / 0 °C

2: mCPBA / CH₂Cl₂ / 0.08 h / Ambient temperature

3: NaI, TFA / 0.17 h / Ambient temperature

4: 1.) DBU, PBu₃, 2.) I₂ / 1.) THF, r.t., 8 h, 2.) CH₂Cl₂, r.t., overnight

With tributylphosphine; iodine; phenyltrimethylammonium tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium iodide; In dichloromethane;
DOI:10.1055/s-1999-3105