Dimethylformamide → HCID 11163965, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyllithium in pentane (1.7 M, 21.8 mL, 37.1 mmol, 2.40 equiv) was added to a solution of tert-butyl 3-{[tert-butyl(dimethyl)silyl]oxy}phenyl carbamate (12-3, 5.00 g, 15.5 mmol, 1 equiv) in ethyl ether (150 mL) at −40° C., and the resulting mixture was stirred at −40° C. for 2 h. N,N-Dimethylformamide (9.57 mL, 124 mmol, 8.00 equiv) was added, and the mixture was then warmed to 0° C. The reaction mixture was partitioned between water (500 mL) and ethyl ether (500 mL). The organic layer was dried over sodium sulfate and concentrated, and the residue was purified by flash column chromatography (hexane, initially, grading to 20% hexane in EtOAc) to give tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-2-formylphenylcarbamate (12-4) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 10.34 (s, 1H), 9.54 (s, 1H), 7.76 (d, 1H, J=1.8 Hz), 7.26 (d, 1H, J=7.8 Hz), 6.35 (dd, 1H, J=7.8, 1.9 Hz), 1.37 (s, 9H), 0.78 (s, 9H), −0.02 (s, 6H).

Provenance & Evidence