Triphenylphosphine → HCID 15341166, compound

Participants

Reaction Steps

To a solution of Intermediate 1 (1.0 g, 3.1 mmol) in THF (25 ml) at RT was added PPh3 (820 mg, 1 eq), 2-indanol (419 mg, 1 eq) and the solution stirred for 10 min prior to the addition of DEAD (492 μl, 1 eq). The reaction mixture was stirred at this temperature for 65 h before the further addition of 2-indanol (419 mg), PPh3 (820 mg) and DEAD (492 μl ). The mixture was stirred for an additional 1.5 h then quenched by the addition of water (10 ml). The mixture was diluted with ethyl acetate (100 ml), washed with water (4×50 ml), brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give a brown foam. The crude product was redissolved in ethyl acetate (50 ml) and extracted into hydrochloric acid (2×50 ml, 10% aq). The aqueous extract was basified (NaOH to pH>10) then extracted with ethyl acetate (2×100 ml). The extract was washed with water (2×50 ml), brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give a white foam. This was subjected to column chromatography (SiO2 ; ethylacetate) to afford the title compound (856 mg, 63%) as a white foam. δH (CDCl3) 3.05-3.35 (6H, m), 3.77 (3H, s), 4.06 (1H, t, J 8.0 Hz), 5.08 (1H, m), 6.52 (2H, d, J 7.8 Hz), 6.63 (1H, d, J 7.6 Hz), 6.70 (1H, s), 6.76 (2H, s), 6.95 (2H, d, J 6.0 Hz), 7.07 (1H, t, J 7.7 Hz), 7.18 (4H, m), and 8.41 (2H, d, J 5.9 Hz). m/z (ESI) 437 (MH+, 100%), 459 (MNa+, 2).

Provenance & Evidence