Nitrogen → HCID 131730010, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole (480 mg, 2.25 mmol) in dry THF (11.0 mL) was treated at −78° C. with a solution of t-butyllithium (1.83 mL of a 1.6M solution in pentane, 2.93 mmol) while keeping the temperature below −70° C. The reaction mixture was then stirred for 1 h at −40° C. N,N-Dimethyl-acetamide (0.42 mL, 4.50 mmol) was added dropwise to the reaction mixture at −78° C. and the reaction mixture was allowed to warm to rt and stirred for 2 h at rt. Water (20 mL) followed by sat. aq. NH4Cl (15 mL) were added. The aq. layer was extracted with EA (2×20 mL) and the combined org. extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (4:1 hept-EA)=0.25. LC-MS-conditions 02: tR=1.05 min; [M+H]+=256.47.

Provenance & Evidence