ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate

Base Information

• Chemical Name: ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate
• CAS No.: 944450-08-2
• Molecular Formula: C₁₄H₂₀O₃
• Molecular Weight: 236.311
• Mol file: 944450-08-2.mol

Synonyms:ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate

Chemical Property of ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate

There total 1 articles about ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate 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: 85.0%

ethyl bromoacetate (105-36-2) + (-)-5-isopropenyl-3-methyl-cyclohex-2-enone (731811-34-0,731811-35-1) → ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate (944450-08-2) + ethyl 2-[(1R,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate

Guidance literature:

(-)-5-isopropenyl-3-methyl-cyclohex-2-enone; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

ethyl bromoacetate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 4.75h; Further stages.;

DOI:10.1021/jo070165r

Reference yield: 72.0%

ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate (944450-08-2) → (1R,5R,6S)-6-(2-hydroxyethyl)-3-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol (944450-09-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -78 - 20 ℃;

DOI:10.1021/jo070165r

Reference yield:

ethyl 2-[(1S,6R)-4-methyl-2-oxo-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetate (944450-08-2) → methyl (6R,2E,4E)-3-(3-(4-methoxybenzyloxy)propyl)-6-hydroxy-4-(2-(triisopropylsilyloxy)ethyl)-7-((1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl)hepta-2,4-dienoate (944450-22-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 72 percent / lithium aluminum hydride / diethyl ether / -78 - 20 °C

2.1: 78 percent / pyridine / 0.5 h / 0 °C

3.1: 96 percent / ethyldiisopropylamine / CH₂Cl₂ / 0 - 20 °C

4.1: 97 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h / -78 °C

5.1: 98 percent / sulfur trioxide-pyridine complex; ethyldiisopropylamine; DMSO / CH₂Cl₂ / 0.67 h / -30 - -15 °C

6.1: 78 percent / Zn(OTf)2; (+)-N-methylephedrine; triethylamine / toluene / 15 h / 20 °C

7.1: tributyltin hydride / dichlorobis[tri(o-tolyl)phosphine]palladium / tetrahydrofuran / 0 - 20 °C

7.2: iodine / diethyl ether / 0.25 h / 0 °C

8.1: tributyltin hydride; lithium diisopropylamide; copper cyanide / tetrahydrofuran; diethyl ether; methanol / 0.25 h / -78 - -25 °C

8.2: 1.56 g / copper(I) chloride / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 10 h / 20 °C

With pyridine; lithium aluminium tetrahydride; tri-n-butyl-tin hydride; copper(l) cyanide; sulfur trioxide pyridine complex; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; 5.1: Parikh-Doering oxidation;

DOI:10.1021/jo070165r

upstream raw materials:

ethyl bromoacetate

(-)-5-isopropenyl-3-methyl-cyclohex-2-enone

Downstream raw materials:

(1R,5R,6S)-6-(2-hydroxyethyl)-3-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethanol

2-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]acetaldehyde

(R)-6-(triisopropylsilyloxy)-1-[(1S,2R,6R)-2-(methoxymethoxy)-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]hex-3-yn-2-ol