6-Methoxy-alpha-tetralone → HCID 18434415, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Bromo-2-(2-pyrrolidin-1-ylethoxy)pyridine (7.0 g, 26 mmol) in dry THF (50 mL) at −78° C. was added n-BuLi (2.5 M in hexanes, 12.4 mL, 31.0 mmol) dropwise. After 30 min, 6-methoxy-1-tetralone (4.55 g, 25.8 mmol) in dry THF was added. After stirring for 15 min at −78° C., the reaction was allowed to warm to room temperature. After 30 min, the reaction was poured into aq NaHCO3 (satd). The aqueous layer was extracted with EtOAc (2x). The combined organic solutions were dried (MgSO4), filtered, and concentrated. Flash chromatography (CHCl3: MeOH, 95:5) provided the alcohol (4.23 g, 44%) as a white solid. 1H NMR (250 MHz, CDCl3): δ8.07 (d, J=2.5 Hz, 1 H), 7.49 (dd, J=2.5, 8.7 Hz, 1 H), 7.00 (d, J=8.5 Hz, 1 H), 6.73 (m, 3 H), 4.45 (t, J=5.7 Hz, 2 H), 3.79 (s, 3 H), 2.92 (t, J=5.7 Hz, 2 H), 2.76 (m, 2 H), 2.67 (m, 4 H), 2.11 (s, 1 H), 2.08 (m, 3 H), 1.82 (m, 5 H).

Provenance & Evidence