Reaction #2139942

Reaction equation

9-anthryl2-propyl hydrogen succinate

9-anthracene methanol

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

9-bromoanthracene

→

1,3-di-(9-anthryl)-2-propyl 9-anthrylmethyl succinate

Yield 70.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherit was partitioned between water and ethyl acetate
2. 2
   WashThe aqueous phase was washed with ethyl acetate twice
3. 3
   Washthe combined organic extracts were washed with saturated ammonium chloride, water, brine
4. 4
   Dryingdried over sodium sulfate
5. 5
   Concentrationconcentrated in vacuo

Procedure

To a mixture of 1,3-di-(9-anthryl2-propyl hydrogen succinate (4) (103.3 mgr, 0.20 mmoles) prepared from 9-bromoanthracene (A. Castellan, L. Kessab, S. Grelier, A. Nourmamode, M. Cotrait, P. Marsau, J. Chem. Soc. Perkin Trans. 2, 1993, 953-961) (scheme 1), and 9-anthracene methanol (60.7 mgr, 0.29 mmoles), in dry dichloromethane (0.2 ml) a catalytic amount of 4-dimethylaminopyridine (4-DMAP) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (42.48 mgr, 0.222 mmoles) was added, at ice bath temperature. The reaction mixture was stirred overnight under argon, at room temperature and then it was partitioned between water and ethyl acetate. The aqueous phase was washed with ethyl acetate twice and the combined organic extracts were washed with saturated ammonium chloride, water, brine, dried over sodium sulfate and concentrated in vacuo. The crude mixture was subjected to flash chromatography to afford 99.4 mgr (70%) of 1,3-di-(9-anthryl)-2-propyl 9-anthrylmethyl succinate which was further purified by recrystallization from dichloromethane (yellow crystals). 1H NMR (250 MHz, CDCl3): δ 8.35 (5H, m), 8.00 (10H, d), 7.50-7.10 (12H, m), 6.10 (2H, s), 5.70 (1H, m), 4.10 (2H, dd), 3.65 (2H, dd), 2.10 (4H, t); 13C NMR (62.5 MHz, CDCl3): δ 131.54, 131.15, 130.38, 129.62, 128.85, 126.92, 125.38, 124.62, 123.85, 63.85, 31.54, 30.38, 29.23, 28.46 ppm; FTIR 3050.0, 2920.0, 1723.9, 1158.7, 891.3, 731.0 cm−1.

Source