Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester

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Chemical Name:Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester
CAS No.:108893-85-2
Molecular Formula:C₂₈H₂₈N₂O₆S₂
Molecular Weight:552.672
Hs Code.:

Synonyms:Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester

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Chemical Property of Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester

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Technology Process of Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester

There total 9 articles about Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl 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: 88.5%

: 113485-06-6
4-(1-Benzenesulfonyl-3-methyl-but-2-enyl)-3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indole

: 108893-85-2
Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester

Guidance literature:: With zinc(II) chloride; In dichloromethane; for 12h; Ambient temperature;
DOI:10.1016/S0040-4039(00)84745-0

Reference yield:

: 35577-89-0
1-[(4-methylbenzene)sulfonyl]-4,5,6,7-tetrahydro-1H-indol-4-one

: 108893-85-2
Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) butyllithium / 1.) THF, -78 deg C, 2 h; 2.) from -78 deg C to 0 deg C, 4 h

2: 86.6 percent / CuCl₂ / aq. acetic acid / 5 h / Heating

3: 1.) butyllithium / 1.) THF, -78 deg C, 1 h; 2.) from -78 deg C to 0 deg C, 3 h

4: 86.7 percent / NaOMe / methanol; tetrahydrofuran / 18 h / 50 °C

5: 96.2 percent / POCl₃ / tetrahydrofuran / 0.5 h / Ambient temperature

6: 1.) NaH / 1.) THF, R_.T_., 12 h ; 2.) R_.T_., 1 h

7: 100 percent / (PhCN)2PdCl₂ / 1,2-dichloro-ethane / 20 h / 70 °C

8: 1.) NH₄OAc; 2.) NaBH₄ / 1.) AcOH, 90 deg C, 1 h; 2.) CH₂Cl₂, MeOH, 0 deg C, 10 min

9: 88.5 percent / ZnCl₂ / CH₂Cl₂ / 12 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; ammonium acetate; sodium methylate; sodium hydride; copper dichloride; zinc(II) chloride; trichlorophosphate; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; acetic acid; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4039(00)84745-0

Reference yield:

: 113485-01-1
4-(1-Benzenesulfonyl-3-methyl-but-3-enyl)-1H-indole

: 108893-85-2
Benzenesulfinic acid (E)-1,1-dimethyl-3-[3-(2-nitro-ethyl)-1-(toluene-4-sulfonyl)-1H-indol-4-yl]-allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96.2 percent / POCl₃ / tetrahydrofuran / 0.5 h / Ambient temperature

2: 1.) NaH / 1.) THF, R_.T_., 12 h ; 2.) R_.T_., 1 h

3: 100 percent / (PhCN)2PdCl₂ / 1,2-dichloro-ethane / 20 h / 70 °C

4: 1.) NH₄OAc; 2.) NaBH₄ / 1.) AcOH, 90 deg C, 1 h; 2.) CH₂Cl₂, MeOH, 0 deg C, 10 min

5: 88.5 percent / ZnCl₂ / CH₂Cl₂ / 12 h / Ambient temperature

With sodium tetrahydroborate; ammonium acetate; sodium hydride; zinc(II) chloride; trichlorophosphate; bis(benzonitrile)palladium(II) dichloride; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1016/S0040-4039(00)84745-0