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

Boiling point:

281.9±50.0 °C(Predicted)

Density 

0.97±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

Appearance

White to off-white Solid

InChI

InChI=1S/C15H27BO3/c1-12(2)9-11(10-13(3,4)17-12)16-18-14(5,6)15(7,8)19-16/h9H,10H2,1-8H3

InChIKey

VOXXPMAJNSVUKJ-UHFFFAOYSA-N

SMILES

C1(C)(C)OC(C)(C)C=C(B2OC(C)(C)C(C)(C)O2)C1

(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol ester Usage And Synthesis

Synthesis

(b) 2,2,6,6-tetramethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran-1-yl 1,2,2,3,3,4,4,4-ninafluorobutane-1-sulfonate (43.8 g, 0.100 mol) was dissolved in anhydrous dimethoxyethane (DME, 500 mL ), bis(pinacolato)diboron (27.9 g, 0.109 mol), 1,1'-bis(diphenylphosphino)ferrocene (1.60 g, 2.90 mmol), and potassium acetate (KOAc, 29.4 g, 0.30 mol) were added sequentially. After degassing by sonication under argon protection, a 1:1 complex of [1,1'-bis(diphenylphosphino)-ferrocene]-palladium(II) dichloride with dichloromethane (2.19 g, 2.68 mmol) was added. The reaction mixture was heated and stirred at 80 °C overnight. After completion of the reaction, it was cooled to room temperature and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: 0-2% ethyl acetate/hexane) to afford (2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid pinacol ester as a white solid (17 g, 64% yield).1H-NMR (CDCl3; 400 MHz): δ 6.40 (t, 1H, J = 1.8 Hz), 1.97 (d, 2H, J = 1.8 Hz), 1.21 (s, 12H), 1.18 (s, 6H), 1.13 (s, 6H).

References

[1] Patent: US2009/105296, 2009, A1. Location in patent: Page/Page column 44

(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)boronic acid, pinacol ester(1142363-56-1)Related Product Information

• 2-bromo-6-(2,2,6,6-tetramethyltetrahydro-pyran-4-yl)pyridin-3-ylamine
• 2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-amine
• 6-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-pyridin-3-ylamine
• 4-cyano-N-(2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxamide
• 2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate
• 5-nitro-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)-pyridine
• 4-cyano-N-(2-(4,4-dimethylcyclohex-1-en-1-yl)-6-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)pyridin-3-yl)- 1H-imidazole-2-carboxamide