Triphenylphosphine → [S]-(-)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propane

Participants

Reaction Steps

The compound [S]-(-)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propane (Compound 12) was prepared in the same manner as Compound 2 in Example 1 but using [R]-3-chloro-1-phenylpropanol (1.0 g, 5.88 mmol), 4-iodo-2-methylphenol (1.38 g, 5.88 mmol), triphenylphosphine (1.54 g, 5.88 mmol) and ethyl azodicarboxylate (0.93 mL, 1.04 g, 5.88 mmol) in THF (15 mL) at room temperature for 15 hours. Workup and purification gave 1.58 g (69%) of Compound 12 as a thick pale yellow liquid: [α]25D +14.97 (c 10.73, CHCl3); 1H NMR (CDCl3, 250 MHz) δ 7.42-7.20 (m, 7H), 6.39 (d, J=8.8 Hz, 1H), 5.34 (dd, J=4.6, 8.8 Hz, 1H), 3.83-3.73 (m, 1H), 3.65-3.55 (m, 1H), 2.55-2.40 (m, 1H), 2.29-2.13 (m, 1H), 2.25 (s, 3H), FTIR (neat) 3050, 3015, 2950, 2900, 1600, 1480 (s), 1460, 1395, 1350, 1300, 1250(s), 1200, 1135 cm-1. Anal C17H20INO; C, H.

Provenance & Evidence