Allyl Alcohol → HCID 21075408, compound

Participants

Reaction Steps

To a solution of Example 55A (456 mg, 1.32 mmol) in anhydrous tetrahydrofuran (18 mL) was added polymer supported triphenylphosphine (659.5 mg, 1.98 mmol), di-tert-butyl azodicarboxylate (455.5 mg, 1.98 mmol), and allyl alcohol (76.6 mg, 1.32 mmol). The reaction mixture was shaken at room temperature for 5 hours. The solution was filtered, dried with silica gel powder (10 g), and purified by flash chromatography eluting with 20% ethyl acetate in hexanes (2 L) to give the title compound (140.8 mg, 28%). MS (ESI) m/z 385.95 (M+H)+; 1H NMR (500 MHz, DMSO-D6) δ ppm 4.71 (d, J=5.62 Hz, 2 H) 4.95 (d, J=5.30 Hz, 2 H) 5.29–5.36 (m, 2 H) 5.40–5.48 (m, 2 H) 6.00–6.16 (m, 2 H) 7.04–7.10 (m, 2 H) 8.20 (d, J=2.50 Hz, 1 H) 8.88 (s, 1 H) 9.05 (s, 1 H) 10.71 (s, 1 H).

Provenance & Evidence