Toluene → HCID 70117062, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.3 mg (0.013 mmol) of 27 in anhydrous toluene (99.7 μL), pyridine (1 μL) and THF (33 μL) was stirred at −78° C. as 0.0156 mmol of Tebbe reagent (31 μL of a 0.5 M solution in toluene) was added by syringe. Reaction was stirred at −78° C. for 2 h, allowed to stir at 40° C. for 2 h then at 0° C. for 1 h. Reaction was quenched with 15% NaOH (25 μL), allowed to stir for ½ h, warmed to rt and passed through a 1″ plug of Celite. The filter was washed with EtOAc and the filtrate was concentrated in vacuo. Purification of the residue on a 1×17 cm column of silica gel using hexanes/EtOAc (2:1) followed by hexanes/EtOAc (4:1) gave 1.3 mg (25%) of 28 as a clear colorless oil and 1.8 mg (34%) of recovered 27. Data for 28: TLC, T-6, Rf0.76. 1H NMR (500 MHz, CDCl3) δ 0.83 (s, 3H, H-18), 2.86 (m, 2H, H-6), 3.33 (d, 1H, J=7.4 Hz, H-17α), 5.03-5.12 (m, 2H,═CH2), 5.04 (s, 2H, benzylic), 5.85-5.93 (m, 1H, —CH═CH2), 6.72 d, 1H, J=2.6 Hz, H-4), 6.79 (dd, 1H, J=8.7, 2.6 Hz, H-2), 7.21 (d, 1H, J=8.7 Hz, H-1), 7.31-7.44 (m, 5H, Ar—H).

Provenance & Evidence