Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester
CAS No.:194468-86-5
Molecular Formula:C₁₅H₁₄O₅S
Molecular Weight:306.339
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

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Chemical Property of Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

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Technology Process of Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

There total 3 articles about Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl 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: 96.0%

: 98-59-9
p-toluenesulfonyl chloride

: 194468-85-4,205673-22-9,205815-42-5
(3aS,6aS)-3-[1-Hydroxy-meth-(Z)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

: 194468-86-5
Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

Guidance literature:: With triethylamine; In dichloromethane; at -30 ℃; for 1h;
DOI:10.1016/S0040-4020(98)00077-5

Reference yield:

: 56487-70-8
(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

: 194468-86-5
Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / NaH / tetrahydrofuran / 20 h / 23 °C

2: 96 percent / Et₃N / CH₂Cl₂ / 1 h / -30 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(98)00077-5

Reference yield:

: 160080-50-2
(3aS,6R,6aR)-6-iodohexahydro-2H-cyclopenta[b]furan-2-one

: 194468-86-5
Toluene-4-sulfonic acid (3aS,6aS)-2-oxo-4,6a-dihydro-3aH-cyclopenta[b]furan-(3E)-ylidenemethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / DBU / tetrahydrofuran / 1.) 50 deg C, 2 h, 2.) 70 deg C, 90 min

2: 78 percent / NaH / tetrahydrofuran / 20 h / 23 °C

3: 96 percent / Et₃N / CH₂Cl₂ / 1 h / -30 °C

With sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(98)00077-5