(2,2,6,6-Tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol ester

Base Information

• Chemical Name: (2,2,6,6-Tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol ester
• CAS No.: 1142363-56-1
• Molecular Formula: C15H27BO3
• Molecular Weight: 266.189
• Mol file: 1142363-56-1.mol

Synonyms:(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol ester;4,4,5,5-tetraMethyl-2-(2,2,6,6-tetraMethyl-3,6-dihydro-2H-pyran-4-yl)-1,3,2-dioxaborolane

Chemical Property of (2,2,6,6-Tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol ester

Chemical Property:

• Boiling Point: 281.9±50.0 °C(Predicted)
• PSA: 27.69000
• Density: 0.97±0.1 g/cm3(Predicted)
• LogP: 3.52170
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99%, ^*data from raw suppliers

(2,2,6,6-Tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid pinacol ester Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2,2,6,6-Tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol ester

There total 4 articles about (2,2,6,6-Tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol 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: 88.0%

2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (1142363-55-0) + bis(pinacol)diborane (73183-34-3) → 2,2,6,6-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1142363-56-1)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 9h; Darkness;

DOI:10.1002/ejoc.202101454

Reference yield:

2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl-4,4,4,4,4,4,4,4,4-nonafluoro-4λ12-but-1,3-diyne-1-sulfonate → 2,2,6,6-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1142363-56-1)

Guidance literature:

With potassium acetate;

Reference yield:

2,2,6,6-tetramethyltetrahydropyran-4-one (1197-66-6) → 2,2,6,6-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (1142363-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1 h / -78 °C

1.2: 18.33 h / -78 - 20 °C

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 9 h / 80 °C / Darkness

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; potassium acetate; diisopropylamine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1002/ejoc.202101454

upstream raw materials:

2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

bis(pinacol)diborane

phorone

2,2,6,6-tetramethyltetrahydropyran-4-one

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