Water → HCID 59142168, compound

Participants

Reaction Steps

To a vigorously stirred suspension of methyltriphenylphosphonium bromide (942 mg; 2.64 mmol) in tetrahydrofuran (6 ml) 1M solution of potassium tert-butoxide in tetrahydrofuran (2.64 ml; 2.64 mmol) was added dropwise at 0° C. To the next flask with a solution of 20 (255 mg; 0.88 mmol) in tetrahydrofuran (1.1 ml) 1M solution of potassium tert-butoxide (0.88 ml; 0.88 mmol) was added. After 20 min. both mixtures were warmed to room temperature and cooled again to 0° C. after 30 min. The solution of enolate of 20 was transferred via cannula to the stirred solution of ylide. After 1 h the mixture was warmed up to room temperature and stirred for next 4 h. Then saturated aqueous solution of NH4Cl (8 ml) and water (30 ml) was added and the mixture was extracted with diethyl ether (3×100 ml). Organic phase was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (2-15% acetone/benzene) to give 172 mg (0.60 mmol; 68% yield) of 6. 1H NMR (400 MHz, CDCl3) δ 0.89 (3H, t, J=6.9 Hz), 1.00 (2H, m), 1.27-1.35 (4H, m), 1.40 (2H, m), 1.48 (2H, m), 2.09 (2H, t, J=7.8 Hz), 3.78 (2H, d, JH-P=21.7 Hz), 3.78 (6H, d, JH-P=11.2 Hz), 5.14 (2H, m); 13C NMR (101 MHz, CDCl3) δ 14.0, 17.2, 22.5, 27.3, 31.7, 36.0, 37.0 (d, JC-P=135 Hz), 52.9 (d, JC-P=6.5 Hz), 115.4, 147.7, 201.8 (d, JC-P=7.0 Hz).

Provenance & Evidence