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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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

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