Triphenylphosphine → HCID 59598938, compound

Participants

Reaction Steps

To a solution of 4-chloro-2-iodo-phenol 4b (20.32 g, 0.08 mol), (1-benzyl-1, 2, 3, 6-tetrahydro-pyridin-4-yl)-methanol (20.5 g, 0.08 mol) and triphenylphosphine (23.58 g, 0.09 mol) in dry THF (150 mL) was added DEAD (17.4 g, 0.09 mol) at 0° C. under nitrogen atmosphere. After addition, the mixture was stirred at room temperature overnight. The mixture was concentrated to dryness and the residue was basified by Na2CO3 solution (10% 100 mL) and extracted with ethyl acetate (100 mL×3). The combined organic layers were washed with water (100 mL×2) and brine (200 mL), dried over Na2SO4, concentrated to dryness. The residue was purified by column on silica gel to afford 1-benzyl-4-(4-chloro-2-iodo-phenoxymethyl)-1,2,3,6-tetrahydro-pyridine 4c (30 g, 86%). 1H NMR (400 MHz, CDCl3): δ 7.73 (d, J=2.4 Hz, 1 H), 7.22-7.38 (m, 6 H), 6.70 (d, J=8.8 Hz, 1 H), 5.82 (s, 1 H), 4.43 (s, 2H), 3.63 (s, 2 H), 3.05 (s, 2 H), 2.67 (t, J=5.6 Hz, 2 H), 2.28 (s, 2 H).

Provenance & Evidence