Reacción #71025

Ecuación de reacción

N2

[5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-methanol

Et3N

CH2Cl2

→

2-(5-chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction mixture was quenched with water (30 mL)
2. 2
   Extracciónextracted with CH2Cl2 (30 mL)
3. 3
   Secadoextracts were dried over MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Otrothe solvents were removed under reduced pressure

Procedimiento

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [5-(2-methyl-[1,3]dioxolan-2-yl)-furan-2-yl]-methanol (3.20 g, 17.37 mmol) in dry CH2Cl2 (32.0 mL) was treated at 0° C. with Et3N (3.14 mL, 22.59 mmol) followed by DMAP (212 mg, 1.74 mmol) and Ms-C1 (1.62 mL, 20.85 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (30 mL), extracted with CH2Cl2 (30 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give 4.49 g of crude 2-(5-chloromethyl-furan-2-yl)-2-methyl-[1,3]dioxolane as an brown oil. The crude material in acetone (43 mL) was treated, under inert atmosphere (N2) with 4-nitro-2H-[1,2,3]triazole (1.97 g, 17.27 mmol), K2CO3 (7.16 g, 51.82 mmol) followed by TBA bromide (1.11 g, 3.45 mmol). The reaction mixture was stirred for 2 days at rt. Water (30 mL), followed by EA (40 mL) was added. The aq. layer was extracted with EA (40 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA) gave the title compound as an orange oil: TLC:rf (60:40 hept-EA)=0.28. LC-MS-conditions 02: tR=0.95 min; [M+H]+=281.01.

Fuente