2-(4,4,5,5-tetramethy-1,3,2-dioxaborolan-2-yl)-3-hexylthiophene-5-carbaldehyde synthesis
- Product Name:2-(4,4,5,5-tetramethy-1,3,2-dioxaborolan-2-yl)-3-hexylthiophene-5-carbaldehyde
- CAS Number:1402132-40-4
- Molecular formula:C17H27BO3S
- Molecular Weight:322.27
291535-21-2
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73183-34-3
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1402132-40-4
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Yield:1402132-40-4 86.3%
Reaction Conditions:
with palladium bis[bis(diphenylphosphino)ferrocene] dichloride;potassium acetate in 1,4-dioxane at 80; for 6 h;Inert atmosphere;
Steps:
4.1.7 2-(4,4,5,5-Tetramethy-1,3,2-dioxaborolan-2-yl)-3-hexylthiophene-5-carbaldehyde22 (10)
A solution of 9 (2.72 g, 10 mmol), bis(pinacolato)diboron (5.08 g, 20 mmol), PdCl2(dppf) (860 mg, 1 mmol), and KOAc (3.94 g, 30 mmol) in degassed 1,4-dioxane (80 ml) was stirred at 80 °C for 6 h under N2. The reaction was quenched by adding water, and extracted by dichloromethane. The organic phase was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (petroleum/dichloromethane=1/3) to give compound 10 (2.78 g, 86.3%) as yellow liquid. MS (EI): m/z=322. 1H NMR (400 MHz, CDCl3) δ: 9.90 (s, 1H), 7.63 (s, 1H), 2.87 (t, 2H), 1.59-1.56 (m, 2H), 1.34 (s, 12H), 1.31-1.29 (m, 6H), 0.87 (t, 3H)
References:
Zhao, Yun;Jiang, Kejian;Xu, Wei;Zhu, Daoben [Tetrahedron,2012,vol. 68,# 44,p. 9113 - 9118]
69249-61-2
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1693-86-3
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222554-30-5
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