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

Base Information

• Chemical Name: 2-[(1S,2R,6R)-2-hydroxy-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethyl pivalate
• CAS No.: 944450-10-6
• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 280.408
• Mol file: 944450-10-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 2-[(1S,2R,6R)-2-hydroxy-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethyl pivalate 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: 78.0%

(1R,5R,6S)-6-(2-hydroxyethyl)-3-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol (944450-09-3) + pivaloyl chloride (3282-30-2) → 2-[(1S,2R,6R)-2-hydroxy-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethyl pivalate (944450-10-6) + C17H28O3 + C22H36O4

Guidance literature:

With pyridine; at 0 ℃; for 0.5h;

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) → 2-[(1S,2R,6R)-2-hydroxy-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethyl pivalate (944450-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / lithium aluminum hydride / diethyl ether / -78 - 20 °C

2: 78 percent / pyridine / 0.5 h / 0 °C

With pyridine; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1021/jo070165r

Reference yield:

(-)-5-isopropenyl-3-methyl-cyclohex-2-enone (731811-34-0,731811-35-1) → 2-[(1S,2R,6R)-2-hydroxy-4-methyl-6-(prop-1-en-2-yl)cyclohex-3-enyl]ethyl pivalate (944450-10-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiHMDS / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 85 percent / tetrahydrofuran; hexane / 4.75 h / -78 - 20 °C

2.1: 72 percent / lithium aluminum hydride / diethyl ether / -78 - 20 °C

3.1: 78 percent / pyridine / 0.5 h / 0 °C

With pyridine; lithium aluminium tetrahydride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/jo070165r

upstream raw materials:

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

pivaloyl chloride

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

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

Downstream raw materials:

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

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