Substitution of hydroxy by iodide in phthalic anhydride protected phenylglycinol
SyntheticPage 613
DOI:
Submitted: July 10, 2013, published: July 12, 2013
Authors
Nikola P. Chmel (N.Chmel@warwick.ac.uk)
Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from
Chemicals
Imidazole (Aldrich)
Triphenylphosphine (Aldrich)
Iodine (Acros)
THF (distilled over potassium)
Procedure
(R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione (1.0 g, 3.7 mmol) was dissolved in dry THF (50 ml) under argon and cooled in an ice/water bath. Imidazole (0.97 g, 14.1 mmol), triphenylphosphine (2.62 g, 10.0 mmol) and iodine (2.44 g, 9.6 mmol) were added in that order. The resulting mixure was stirred for 1 h at 0°C and then at ambient temperature for 2 d. The reaction was quenched with a saturated solution of sodium thiosulphate (40 ml) and brine (40 ml). The aqueous layer was extracted with DCM (30 ml) and the combined organic layers were dried over anhydrous magnesium sulphate. The solvents were removed under reduced pressure and the residue was purified on silica using DCM as eluent. Product used as is without further purification. Yield 0.5 g (<37%).
Author Comments
Data
1H NMR (400 MHz, 298 K, CDCl3) δH 7.89 – 7.81 (2H, m, Pht), 7.78 – 7.68 (2H+, m, Pht+P(O)Ph3), 7.57 – 7.48 (2H+, m, Ph+ P(O)Ph3), 7.48 – 7.40 (3H, m, Ph), 7.39 – 7.28 (3H, m), 5.56 (1H, dd, 3JHH = 11.5 Hz, 2JHH = 5.3 Hz, CH2), 4.53 (1H, dd, 3JHH = 11.4 Hz, 3JHH = 10.4 Hz, CH), 3.84 (1H, dd, 3JHH = 10.3 Hz, 2JHH = 5.3 Hz, CH2).
MS (ESI+) m/z 250.1 ([M-I]+)
IR (cm-1) ν 3457, 1772, 1700, 1611, 1495, 1467, 1388, 1358, 1266, 1185, 1172, 1120, 1065, 1040, 1013, 999, 877, 838, 793, 765, 719, 698
Lead Reference
Supplementary Information
Keywords
alcohols, amines, aromatics/arenes, Iodination, phthalic anhydride, protecting group, substitution