4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)CYCLOHEX-3-ENE-1-CARBOXYLIC ACID ETHYL ESTER Chemical Properties

Boiling point:

312.6±52.0 °C(Predicted)

Density 

1.03

storage temp. 

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

form 

Liquid

color 

Colorless to light yellow

InChI

InChI=1S/C15H25BO4/c1-6-18-13(17)11-7-9-12(10-8-11)16-19-14(2,3)15(4,5)20-16/h9,11H,6-8,10H2,1-5H3

InChIKey

ZREZDODZGZVRBD-UHFFFAOYSA-N

SMILES

C1(C(OCC)=O)CCC(B2OC(C)(C)C(C)(C)O2)=CC1

Safety Information

HS Code 

2931900090

4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)CYCLOHEX-3-ENE-1-CARBOXYLIC ACID ETHYL ESTER Usage And Synthesis

Uses

4-(Ethoxycarbonyl)cyclohexene-1-boronic acid, pinacol ester

Synthesis

Ethyl 4-((trifluoromethanesulfonyl)oxy)-3-cyclohexene-1-carboxylate (303 mg, 1 mmol) and pinacol ester of bis(boronic acid) (370 mg, 1.5 mmol) were added to KOAc (400 mg, 4 mmol) and Pd(dppf)Cl2 (10 mg, 0.05 mmol) in dioxane (5 mL). The reaction mixture was heated at 110 °C for 16 hours. After completion of the reaction, it was cooled to room temperature and the mixture was partitioned between EtOAc (10 mL) and saturated NaHCO3 solution (10 mL). The aqueous phase was extracted with EtOAc (10 mL × 2). The combined organic phases were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. Purification by fast chromatography (25% EtOAc in petroleum ether solution) afforded ethyl 4-boronic acid pinacol ester-3-cyclohexenecarboxylate (250 mg, 89% yield).LRMS m/z (M + H)+: 281 (measured value), 281 (calculated value).

References

[1] Patent: WO2014/81619, 2014, A1. Location in patent: Page/Page column 128
[2] Patent: US2011/251183, 2011, A1. Location in patent: Page/Page column 18
[3] Patent: US2011/263578, 2011, A1. Location in patent: Page/Page column 34
[4] Patent: WO2011/128265, 2011, A1. Location in patent: Page/Page column 34
[5] Patent: US2011/275801, 2011, A1. Location in patent: Page/Page column 49

4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)CYCLOHEX-3-ENE-1-CARBOXYLIC ACID ETHYL ESTER(1049004-32-1)Related Product Information

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• 3-Methoxybenzylboronic acid pinacol ester