Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-ethyl ester

Base Information

• Chemical Name: Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-ethyl ester
• CAS No.: 141556-73-2
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.45

Synonyms:Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-ethyl ester

Chemical Property of Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-ethyl ester

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Technology Process of Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-ethyl ester

There total 6 articles about Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-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: 51.0%

benzoyl chloride (98-88-4) + 2-((1S,2R,6S,9S,12R)-12-Methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.01,6]tridec-2-yl)-ethanol (141556-66-3,151121-09-4) → Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.01,6]tridec-2-yl)-ethyl ester (141556-73-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.5h;

DOI:10.1021/jm00091a014

Reference yield:

3-{(1S,3R)-3-(2-Hydroxy-ethyl)-2-[1-methoxy-meth-(E)-ylidene]-cyclohexyl}-propionitrile (141556-70-9,141611-18-9,151121-06-1) → Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.01,6]tridec-2-yl)-ethyl ester (141556-73-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / diethyl ether / a) -78 deg C, 10 min, b) -78 deg C to RT, 30 min, c) RT, 15 h

2: methylene blue, O₂ / CH₂Cl₂ / 4 h / -78 °C / Irradiation

3: 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, -78 deg C to RT, 4 h

4: 64 percent / n-Bu₄NF / tetrahydrofuran / 10 h / Ambient temperature

5: 51 percent / Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; oxygen; methylene blue; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm00091a014

Reference yield:

4-{(1R,3S)-3-(2-Hydroxy-ethyl)-2-[1-methoxy-meth-(E)-ylidene]-cyclohexyl}-butan-2-one (141556-71-0,151121-07-2) → Benzoic acid 2-((1S,2R,6S,9S,12R)-12-methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.01,6]tridec-2-yl)-ethyl ester (141556-73-2)

Guidance literature:

Multi-step reaction with 4 steps

1: methylene blue, O₂ / CH₂Cl₂ / 4 h / -78 °C / Irradiation

2: 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, -78 deg C to RT, 4 h

3: 64 percent / n-Bu₄NF / tetrahydrofuran / 10 h / Ambient temperature

4: 51 percent / Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

With tetrabutyl ammonium fluoride; oxygen; methylene blue; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm00091a014

upstream raw materials:

benzoyl chloride

2-((1S,2R,6S,9S,12R)-12-Methoxy-9-methyl-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-2-yl)-ethanol

3-{(1S,3R)-3-(2-Hydroxy-ethyl)-2-[1-methoxy-meth-(E)-ylidene]-cyclohexyl}-propionitrile

4-{(1R,3S)-3-(2-Hydroxy-ethyl)-2-[1-methoxy-meth-(E)-ylidene]-cyclohexyl}-butan-2-one

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