Sodium Bicarbonate → HCID 18434416, compound

Participants

Reaction Steps

Pyridinium bromide perbromide (3.5 g, 12.2 mmol) was added to a solution of 6-methoxy-1-[6-(2-pyrrolidin-1-ylethoxy)pyridin-3-yl]-1,2,3,4-tetrahydronaphthalen-1-ol (3.3 g, 8.9 mmol) in CH2Cl2 (50 mL). The reaction was stirred for 18 h and aqueous NaHCO3 (satd) was added. The aqueous layer was extracted with CH2Cl2 and the combined organic solution was washed with water and brine. The organic solution was dried (MgSO4), filtered, and concentrated. Flash chromatography (CHCl3: MeOH, 95:5) provided the desired vinyl bromide (2.65 g, 70%). 1H NMR (250 MHz, CDCl3): δ8.0 (d, J=2.4 Hz, 1 H), 7.41 (dd, J=2.4, 8.4 Hz, 1 H), 6.83 (d, J=8.4 Hz, 1 H), 6.69 (m, 1 H), 6.55 (m, 2 H), 4.92 (t, J=5.8 Hz, 2 H), 3.76 (s, 3 H), 2.94 (m, 6 H), 2.64 (m, 4 H), 1.82 (m, 4 H).

Provenance & Evidence