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-Cl (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. 150 mg of this crude material in acetone (2.0 mL) was added, under inert atmosphere (N2) to a solution of 4-nitro-1H-pyrazole (87 mg, 0.77 mmol) in acetone (2.0 mL). K2CO3 (320 mg, 2.13 mmol) followed by TBA bromide (50 mg, 0.15 mmol) were added and the reaction mixture was stirred at rt overnight. Water (10 mL) and EA (10 mL) were added. The aq. layer was extracted with EA (10 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 (40:60 hept-EA) gave the title compound as a yellow oil. TLC: rf (40:60 hept-EA)=0.27. LC-MS-conditions 02: tR=0.82 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-ffa34642b79b493ba3029cd7e04f7939

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288419B2