Molecules 1999, 4, M100

Methyl 2-Benzyl-3-phenyl-2-(phenylsulfonyl)propanoate

Mohammed Ramdania*, André Loupyb and Alain Petitb

aLaboratoire de chimie organique et physique, Université Mohamed 1er, Faculté des sciences, Oujda, Maroc. Fax (212)6 74 47 49 E-mail: [email protected]
bLaboratoire des réactions sélectives sur supports, CNRS, UA 478, ICMO, Université Paris XI, bâtiment 410, 91405 Orsay cédex, France. Fax (33) 1 69 15 46 79 E-mail: [email protected]

Received: 28 June 1999 / Accepted: 2 July 1999 / Published: 20 August 1999
 
 

The product 2 was prepared from methyl phenylsulfonyl acetate in situ by the solid-liquid PTC conditions without solvent [1-2]. To ester 1 (0.535 g, 2.5 mmol), was added benzyl chloride (0.791 g, 6.25 mmol), tBuOK (0.701 g, 6.25 mmol) and 10 % of TBAB (tetrabutylammonium bromide) phase transfer catalyst (80 mg, 0.25 mmol). The reaction was carried out under ambient temperature with magnetic agitation during 1 min. An approximate temperature of 95°C was measured at the end of the reaction. The mixture was allowed to cool to ambient temperature. After dilution with ethyl acetate (30 ml) and subsequent filtration through FlorisilTM, the organic product was analysed by GC (using an internal standard) and purified by chromatography on silica gel (pentane: ethyl acetate, 95 : 5), yield: 88 % of isolated product 2.

1H NMR (CDCl3): 3.48 (s, 4H); 3.68 (s, 3H); 7.10-7.23 (m, 10H); 7.48-7.82 (m, 5H).

13C NMR (CDCl3): 165 (ester).

IR (Nujol): 1740 (CO2); 1310 and 1140 cm-1 (SO2).

MS (IC-NH3, m / z): 412 (M+ + 18) / 29.3 %; 272 (M+ - PhSO2 + 18) / 100%.

References

1. Fujii, M.; Nakamura, K.; Mekata, H.; Oka, S.; Ohno, A. Bull. Chem. Soc. Jpn. 1988, 61, 495-500.

2. Yuliang, W.; Yaozhng, J. Synth. Commun. 1992, 22, 2287-2291.

Sample Availability: Available from the authors.

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