Diethyl Ether → HCID 58730937, compound

Participants

Reaction Steps

To a stirred and cooled (−78° C.) solution of the bromide 4 (100 mg, 0.32 mmol) in Et2O (1.8 mL) was added dropwise 1.5 M solution of tert-butyllithium in pentane (0.45 mL, 0.67 mmol). The mixture was stirred for an additional 0.6 h at −78° C., p-tolylaldehyde (0.04 mL, 0.32 mmol) was added, and the mixture slowly allowed to warm to r.t. After 18 h the mixture was partitioned between AcOEt-brine. The aqueous layer was extracted with AcOEt (2×). The combined organic solutions were dried (MgSO4), concentrated, and the residue was purified by PTLC with CH2Cl2:MeOH=95:5 as eluent to afford alcohol 19 (15 mg, 19%) as a white solid. 1H NMR (400 MHz; CDCl3) δ 2.34 (s, 3H), 5.99 (s, 1H), 6.45 (d, J=3.5 Hz, 1H), 7.16 (d, J=7.8 Hz, 2H), 7.30-7.32 (m, 3H), 7.93 (d, J=1.8 Hz, 1H), 8.32 (d, J=2.0 Hz, 1H) and 9.77 (br s, NH).

Provenance & Evidence