Cyclopropanol, 1-ethenyl-, 4-methylbenzenesulfonate

Base Information

• Chemical Name: Cyclopropanol, 1-ethenyl-, 4-methylbenzenesulfonate
• CAS No.: 32364-41-3
• Molecular Formula: C12H14O3S
• Molecular Weight: 238.307
• Mol file: 32364-41-3.mol

Synonyms:

Chemical Property of Cyclopropanol, 1-ethenyl-, 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopropanol, 1-ethenyl-, 4-methylbenzenesulfonate

There total 6 articles about Cyclopropanol, 1-ethenyl-, 4-methylbenzenesulfonate 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: 93.0%

1-Ethenylcyclopropan-1-ol (22935-31-5) + p-toluenesulfonyl chloride (98-59-9) → 1-tosyloxy-1-vinylcyclopropane (32364-41-3)

Guidance literature:

With pyridine; at 0 ℃; for 14h;

DOI:10.1021/ja00037a006

Reference yield: 64.0%

1-ethoxy-1-cyclopropanol (13837-45-1) + vinyl magnesium bromide (1826-67-1) + p-toluenesulfonyl chloride (98-59-9) → 1-tosyloxy-1-vinylcyclopropane (32364-41-3)

Guidance literature:

1-ethoxy-1-cyclopropanol; vinyl magnesium bromide; In tetrahydrofuran; at 0 ℃; for 4h; Inert atmosphere; Reflux;

p-toluenesulfonyl chloride; In tetrahydrofuran; at 0 ℃; for 14h; Inert atmosphere;

DOI:10.1021/ol5015224

Reference yield:

Toluene-4-sulfonic acid 1-ethynyl-cyclopropyl ester → 1-tosyloxy-1-vinylcyclopropane (32364-41-3)

Guidance literature:

With quinoline; hydrogen; Pd-BaSO₄; BaSO₄ deactivated with lead; In dichloromethane; for 24h; Yield given; Ambient temperature;

upstream raw materials:

1-Ethenylcyclopropan-1-ol

p-toluenesulfonyl chloride

(2-cyclopropylethynyl)trimethylsilane

Toluene-4-sulfonic acid 1-trimethylsilanylethynyl-cyclopropyl ester

Downstream raw materials:

(3-(2-cyclopropylideneethoxy)prop-1-yn-1-yl)benzene

diethyl 2-(2-cyclopropylideneethyl)-2-(3-phenylprop-2-ynyl)malonate

N-(2-cyclopropylideneethyl)-4-methyl-N-(4-phenylbut-3-yn-1-yl)benzenesulfonamide

N-(but-2-yn-1-yl)-N-(2-cyclopropylideneethyl)-4-methylbenzenesulfonamide

Refernces

• 1、 Kim, Seyun,Chung, Young Keun. "Rhodium-catalyzed carbonylative [3 + 2 + 1] cycloaddition of alkyne-tethered alkylidenecyclopropanes to phenols in the presence of carbon monoxide". supporting information. p. 4352 - 4355. Retrieved 2015/01/09.
• 2、 Stolle, Andreas,Ollivier, Jean,Piras, Pier Paolo,Salaün, Jacques,De Meijere, Armin. "Nucleophilic substitutions of 1-alkenylcyclopropyl esters and 1-alkynylcyclopropyl chlorides catalyzed by palladium(0)". . p. 4051 - 4067. Retrieved 2007/10/02.