Nitrogen → (5-Methanesulfonyl-furan-2-yl)-methanol

Participants

Reaction Steps

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-carboxylic acid ethyl ester (1.26 g) in THF (57.0 mL) was treated at −78° C. with DiBAL (19.50 mL of a 1M solution in THF, 19.50 mmol) and the reaction mixture was stirred at this temperature for 2 h. The reaction mixture was poured on Rochelle's salt (100 mL) and stirred at rt for 12 h. The aq. layer was extracted with EA (2×100 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (30:70 hept-EA) gave the title compound as a yellow oil. TLC: rf (30:70 hept-EA)=0.28. LC-MS-conditions 02: tR=0.50 min.

Provenance & Evidence