My PhD dissertation - Institut Fresnel

80
C13H13NO2 (215.25) calcd. C 72.54% H 6.09%
found C 71.55% H 6.03%.
Ethyl bis{N-[(1S)-phenylethyl]pyrrol-2-yl}phosphinite (19): At -75 °C, butyllithium
(20 mmol) in hexanes (13 mL) was added to a solution of (-)-(1S)-2-bromo-
N-(1-phenylethyl)pyrrole (17; 5.0 g, 20 mmol) in toluene (20 mL). The reaction mixture was
kept at - 10 °C for 20 min. Triethyl phosphite (1.7 mL, 1.7 g, 10 mmol) was then added over a
period of 20 min and the solution was kept at 25 °C for 3 h. The volatiles were then
evaporated to leave an orange oil. Purification by column chromatography on silica (0.16 kg)
eluted with a 5 : 95 (v/v) mixture of ethyl acetate and hexanes afforded a pale yellow liquid;
yield: 1.89 g (47%).
1 H NMR: δ = 7.2 (m, 6 H), 7.1 (m, 4 H), 7.01 (dd, J = 3.6, 2.1 Hz, 1 H), 6.8 m,
1H), 6.41 (symm. m, 1 H), 6.30 (dd, J = 3.0, 1.5 Hz, 1 H), 6.20 (symm. m, 1 H),
6.2 (m, 1 H), 5.92 (qd, J = 6.6, 5.1 Hz, 1 H), 5.49 (quint, J = 6.6 Hz, 1 H), 3.55
(symm. m, 2 H), 1.73 (d, J = 6.6 Hz, 3 H), 1.61 (d, J = 6.6 Hz, 3 H), 0.94 (t, J =
6.7 Hz, 3 H) ppm.
31 P NMR: δ = 143.5 ppm.
MS : 416 (23%, M + +1), 105 (100%), 77 (24%).