Triphenylphosphine → HCID 10023063, compound

Participants

Reaction Steps

The compound [R]-(+)-1-chloro-3-phenyl-3-(4-iodo-2-methylphenoxy)propane (Compound 5) was prepared in the same manner as for the preparation of Compound 2 in Example 1, but using [S]-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 1.60 g (70%) of Compound 5 as a thick pale yellow liquid: [απ25D +14.02 (c 7.7, CHCL3); 1H NMR (CDCl3, 250 MHz) δ 7.41-7.20 (m, 7H), 6.39 (d, J=8.8 Hz, 1H), 5.34 (dd, J=4.4, 8.8 Hz, 1H), 3.81-3 72 (m, 1H), 3.63-3.55 (m, 1H), 2.55-2.41 (m, 1H), 2.31-2.16 (m, 1H), 2.7 (s, 3H); FTIR (neat) 3080, 3020, 2970, 2915, 1585, 1485(s), 1450, 1390, 1360, 1290, 1245(s), 1180, 1130 cm-1. Anal. C17H20INO: C,H.

Provenance & Evidence