Allyl iodide → HCID 54574304, compound

Participants

Reaction Steps

Combine (S)-4-benzyl-3-phenylacetyl-2-oxazolidinone (14.13 g, 47.9 mmol) and tetrahydrofuran (150 mL). Cool in a dry-ice/acetone bath. Add dropwise a solution of sodium bis(trimethylsilyl)amide (52.6 mL, 1.0 M in tetrahydrofuran, 52.6 mmol). After 25 minutes, add allyl iodide (13.12 mL, 143.5 mmol) and then replace the bath with a dry-ice/carbon tetrachloride bath. After 1 hour, quench the reaction by the addition of a saturated aqueous ammonium chloride solution, extract with diethyl ether, and separate the layers. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 15% ethyl acetate/hexane. Combine the product containing fractions, evaporate, and recrytallize from chloroform/hexane to give (S)-4-benzyl-3-(2-phenylpent-4-enoyl)-2-oxazolidinone: Rf=0.40 (silica gel, 15% ethyl acetate/hexane).

Provenance & Evidence