3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester

Base Information

• Chemical Name: 3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester
• CAS No.: 299185-07-2
• Molecular Formula: C₂₆H₃₂O₅SSi
• Molecular Weight: 484.689

Synonyms:3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester

Chemical Property of 3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester

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Technology Process of 3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester

There total 1 articles about 3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl 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: 58.0%

2-(chloromethyl)-3-(phenylsulfonyl)-1-propene (116830-92-3) + 4-(tert-butyl-dimethyl-silanyloxy)-but-2-ynoic acid phenyl ester → 3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester (299185-07-2)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; In tetrahydrofuran; hexane; at -60 ℃; for 4h;

DOI:10.1016/S0040-4039(00)00867-4

Reference yield: 89.0%

3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester (299185-07-2) → 4-benzenesulfonyl-5-methylene-3,4,5,6-tetrahydro-cyclopenta[c]furan-1-one (299185-20-9)

Guidance literature:

3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester; With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 4h;

toluene-4-sulfonic acid; In benzene; for 2h; Heating;

DOI:10.1016/S0040-4039(00)00867-4

Reference yield:

3-benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylene-cyclopent-1-enecarboxylic acid phenyl ester (299185-07-2) → 4-benzenesulfonyl-5-methyl-3,6-dihydro-cyclopenta[c]furan-1-one

Guidance literature:

Multi-step reaction with 2 steps

1.1: HCl / tetrahydrofuran / 4 h / 20 °C

1.2: 89 percent / p-TSA / benzene / 2 h / Heating

2.1: Na₂CO₃ / H₂O; tetrahydrofuran / 1 h / 20 °C

With hydrogenchloride; sodium carbonate; In tetrahydrofuran; water; 1.1: Hydrolysis / 1.2: Cyclization / 2.1: Rearrangement;

DOI:10.1016/S0040-4039(00)00867-4

upstream raw materials:

2-(chloromethyl)-3-(phenylsulfonyl)-1-propene

Downstream raw materials:

4-benzenesulfonyl-5-methylene-3,4,5,6-tetrahydro-cyclopenta[c]furan-1-one

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