Nitrogen → 2-Chloromethyl-5-methanesulfonyl-furan

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (5-methanesulfonyl-furan-2-yl)-methanol (692 mg, 3.93 mmol) in dry CH2Cl2 (7.0 mL) was treated at 0° C. with Et3N (0.71 mL, 5.11 mmol) followed by DMAP (50 mg, 0.39 mmol) and Ms-C1 (0.37 mL, 4.71 mmol). After stirring at rt for 2 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (20 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give 868 mg of crude 2-chloromethyl-5-methanesulfonyl-furan as a yellow oil. 183 mg of this crude material in DMF (0.7 mL) was added to a solution of 4-nitro-2H-[1,2,3]triazole (90 mg, 0.79 mmol) in DMF (0.7 mL) pre-treated for 1 h with DIPEA (0.27 mL, 1.59 mmol) and the reaction mixture was stirred for 48 h at rt. Water (10 mL), followed by EA (10 mL) were added. The aq. layer was extracted with EA (10 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 (4:6 hept-EA) gave the title compound as a yellow oil: TLC:rf (4:6 hept-EA)=0.36. LC-MS-conditions 02: tR=0.85 min.

1. customthe reaction mixture was quenched with water (10 mL)
2. extractionextracted with CH2Cl2 (20 mL)
3. dry with materialextracts were dried over MgSO4
4. filtrationfiltered
5. customthe solvents were removed under reduced pressure

ORD record

ord-d8397f3d0bce4a9b9b9b346675706e98

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536209B2