Diethylamine → HCID 15199167, compound

Participants

Reaction Steps

Vinyl bromide (0.5 mL, excess) was condensed into a flask under argon, followed by addition of CuI (7.2 mg, 0.015 mmol), (Ph3P)2PdCl2 (26 mg, 0.0376 mmol) and Et2NH (3 mL). Compound 10 (145 mg, 0.376 mmol) in benzene (10 mL) was added at 5° C. and the mixture was stirred in the dark for 16 h. Benzene was removed in vacuo, the residue was dissolved in CH2Cl2 (10 mL), washed with NH4Cl solution (2×15 ml) and water (15 mL), dried (MgSO4), concentrated in vacuo, and the residue purified by flash column chromatography (1:5 CH2Cl2 :hexanes) giving 11 as a yellow-green oil (109 mg, yield 70%): EI-MS, m/z 410 (M+), NH3CI-MS, m/z 428 (MNH4 +); UV (CH2Cl2) λ max 403; IR (CH2Cl2) 2226 (m), 2193 (w), 2142 (w) (all C=C), 1602 (m, C=C) cm-1 ; 1H NMR δ 7.1-7.3 (m, 10H), 6.95 (d, J=17.7, 2.1 Hz, 1 H), 5.49 (dd, J=11.1, 2.1 Hz, 1 H), 4.03 (s, 2 H), 4.02 (s, 2 H), 1.96 (s, 3 H); 13C NMR δ 116-138 (several), 94.90, 88.69, 84.46, 80.94, 72.69, 64.46, 37.52, 4.99.

Provenance & Evidence