Nitrogen → HCID 21972708, compound

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(5-hydroxymethyl-furan-2-yl)-ethanone (2.00 g, 14.27 mmol) in dry CH2Cl2 (29 mL) was treated at 0° C. with Et3N (2.58 mL, 18.55 mmol) followed by DMAP (178 mg, 1.43 mmol) and Ms-Cl (1.33 mL, 17.13 mmol). After stirring at rt for 3 h, the reaction was quenched with water. The layers were separated and the aq. layer extracted with CH2Cl2 (3×) The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give 3.93 g (quant.) of crude 1-(5-chloromethyl-furan-2-yl)-ethanone as a brown oil. Part of this crude material (1.718 g, 10.83 mmol) in DMF (10.3 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (10.30 g of a 10% solution in acetone, 9.03 mmol) in DMF (10.3 mL) pre-treated for 30 min with DIPEA (3.09 mL, 18.06 mmol) and the reaction mixture was stirred overnight at 50° C. Water (32 mL), followed by EA (65 mL) were added. The aq. layer was extracted with EA (65 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (2:1 hept-EA) gave the title compound as a yellow solid: TLC:rf (2:1 hept-EA)=0.20. LC-MS-conditions 02: tR=0.85 min, [M+H]+=237.46.

1. customthe reaction was quenched with water
2. customThe layers were separated
3. extractionthe aq. layer extracted with CH2Cl2 (3×) The org
4. dry with materiallayer was dried over MgSO4
5. filtrationfiltered
6. customthe solvents were removed under reduced pressure

ORD record

ord-61492e4edbd74c4ab292dbec0f64616c

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580831B2