2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester

Base Information

Chemical Name:2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester
CAS No.:528607-29-6
Molecular Formula:C₁₈H₂₆O₅S
Molecular Weight:354.467
Hs Code.:

Synonyms:2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester

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Chemical Property of 2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester

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Technology Process of 2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester

There total 7 articles about 2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl 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: 84.0%

: 98-59-9
p-toluenesulfonyl chloride

: 528607-26-3
2-(3-hydroxypropyl)-2-ethylcyclopropanecarboxylic acid ethyl ester

: 528607-29-6
2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 4 ℃; for 48h;
DOI:10.1039/b209992f

Reference yield:

: 2955-62-6
methyl 4-oxohexanoate

: 528607-29-6
2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaHMDS / tetrahydrofuran / 1.5 h / 18 °C

1.2: 30 percent / tetrahydrofuran / 15 h / 18 °C

2.1: 57 percent / LiAlH₄ / diethyl ether / 1.5 h

3.1: 70 percent / NaH; NaI / dimethylformamide / 18 h / 18 °C

4.1: Rh₂(OAc)4 / CH₂Cl₂ / 0.5 h / 18 °C

5.1: 210 mg / H₂ / 5percent Pd/C / CH₂Cl₂; ethyl acetate; ethanol / 22 h / 18 °C / 760.05 Torr

6.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h / 4 °C

With dmap; lithium aluminium tetrahydride; hydrogen; sodium hexamethyldisilazane; sodium hydride; triethylamine; sodium iodide; dirhodium tetraacetate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.2: Wittig reaction;
DOI:10.1039/b209992f

Reference yield:

: 13064-28-3
methyl 4-nitrohexanoate

: 528607-29-6
2-ethyl-2-[3-(toluene-4-sulfonyloxy)propyl]cyclopropanecarboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 95 percent / aq. NaHCO₃; K₂CO₃; Oxone / acetone / 29 h / 18 °C

2.1: NaHMDS / tetrahydrofuran / 1.5 h / 18 °C

2.2: 30 percent / tetrahydrofuran / 15 h / 18 °C

3.1: 57 percent / LiAlH₄ / diethyl ether / 1.5 h

4.1: 70 percent / NaH; NaI / dimethylformamide / 18 h / 18 °C

5.1: Rh₂(OAc)4 / CH₂Cl₂ / 0.5 h / 18 °C

6.1: 210 mg / H₂ / 5percent Pd/C / CH₂Cl₂; ethyl acetate; ethanol / 22 h / 18 °C / 760.05 Torr

7.1: 84 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h / 4 °C

With dmap; Oxone; lithium aluminium tetrahydride; hydrogen; sodium hexamethyldisilazane; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; sodium iodide; dirhodium tetraacetate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; 1.1: Nef reaction / 2.2: Wittig reaction;
DOI:10.1039/b209992f