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Protection of phenyl glycinol using phthalic anhydride; (R)-2-(2-hydroxy-1-phenylethyl)isoindoline-1,3-dione

SyntheticPage 609
DOI: 10.1039/SP609
Submitted Jul 10, 2013, published Jul 12, 2013
Nikola P. Chmel (N.Chmel@warwick.ac.uk), Pratik Gurnani (pratik.gurnani@warwick.ac.uk)
A contribution from Scott group, Warwick University


			Reaction Scheme: <img src="/images/empty.gif" alt="" />Protection of phenyl glycinol using <span id="csm1374586974145" class="csm-chemical-name" title="phthalic anhydride">phthalic anhydride</span><img src="/images/empty.gif" alt="" />

Chemicals Used

(R)-phenylglycinol (Prepared in house, See page 275)
Phthalic anhydride (Aldrich)
Dichloromethane (Fisher Scientific)

Procedure

Solid (R)-phenylglycinol (2.0 g, 14.5 mmol) and phthalic anhydride (2.16 g, 14.5 mmol) were heated with stirring to 145°C for 4 h. The obtained yellow oil was dissolved in DCM (50 ml) and the solution was dried over anhydrous sodium sulphate. The solvent was then removed under reduced pressure and the product was used in the subsequent step without further purification. Yield 3.7 g (95%).

Author's Comments

Worked smoothly and reproducibly

Data

1H NMR (400 MHz, 298 K, CDCl3) δH 7.83 – 7.74 (2H, m, Pht), 7.70 – 7.60 (2H, m, Pht), 7.49 (2H, d, 3JHH = 7.4 Hz, Ph), 7.41 – 7.23 (3H, m, Ph), 5.51 (1H, dd, 3JHH = 8.9 Hz, 3JHH = 5.0 Hz, CH), 4.76 – 4.66 (1H, m, CH2), 4.24 (1H, dd, 3JHH = 11.4 Hz, 4JHH = 4.9 Hz, CH2), 3.47 (1H, s, OH).

13C NMR (100 MHz, 298 K, CDCl3) δC 168.89 (C=O), 136.88, 134.08 (Pht), 131.72, 128.70, 128.13, 127.97 (Ph), 123.31 (Pht), 61.98 (CH2), 57.46 (CH).

MS (ESI+) m/z 290.1 ([M+Na]+)

IR (cm-1) ν 3457, 1772, 1700, 1611, 1585, 1495, 1467, 1388, 1358, 1332, 1288, 1266, 1185, 1172, 1120, 1065, 1040, 1013, 999, 962, 919, 877, 838, 793, 765, 719, 698.


Lead Reference

M. D. Chen, M. Z. He, X. Zhou, L. Q. Huang, Y. P. Ruan and P. Q. Huang, Tetrahedron, 2005, 61, 1335-1344 http://dx.doi.org/10.1016/j.tet.2004.10.109

Supplementary Information

1H NMR (1H NMR.jcamp)
13C NMR (13C NMR.jcamp)
Infrared (IR.asc)

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Keywords: addition, alcohols, amines, phenyl glycinol, phthalic anhydride

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