Sodium hydride → 4-(Bis-benzyloxy-phosphoryl)-butyric acid ethyl ester

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Reaction Steps

To a suspension of NaH (60%, 2.52 g, 63 mmol) in DMF (60 mL) was added dibenzyl phosphite (12 mL, 48.45 mmol). After 15 minutes of stirring, ethyl-4-bromobutyrate was added and the mixture was stirred for 48 h at room temperature. The DMF was removed by evaporation. The residue was partitioned between brine, ammonium chloride and ether. The water phase was extracted several times with ether. The recombined organic layer was extracted with brine, dried over sodium sulfate, filtered and evaporated. The residue was flashed using 50% ethyl acetate in hexanes to afford the product as a colorless oil. 1H-NMR(CDCl3, 400 MHz: 1.23(t, J=7.2 Hz, 3H); 1.77-2.04(m, 4H); 2.37(m, 2H); 4.10(q, J=7.2 Hz, 2H), 5.03(m, 4H); 7.31(m, 10H). 31P-NMR(CDCl3, 400 MHz): 32.78.

Provenance & Evidence