Ethyl 3-iodopropionate

Ethyl 3-iodopropionate Propanoic acid, 3-iodo-, ethyl ester (9) (6414-69-3)... 

ETHYL 3-(p-CYAN0PHENYL)PR0PI0NATE FROM ETHYL 3-IODOPROPIONATE AND p-CYANOPHENYLZINC BROMIDE... 

A. Ethyl 3-iodopropionate. A 1-L, round-bottomed flask equipped with a magnetic stirring bar and a reflux condenser is charged with ethyl 3-chloropropionate (27.3 g, 0.2 mol) (Note 1) and acetone (400 mL). Sodium iodide (300 g, 2 mol) (Note 2) is added to the clear solution and the mixture is refluxed for 16 hr. The resulting pale yellow reaction mixture is cooled to room temperature, the stirring bar and reflux condenser are removed and the acetone is removed on a rotary evaporator at 40°C/550 mbar (412 mm). The residue is taken up in diethyl ether (300 mL) and washed with a saturated aqueous solution of sodium... 

DeCamp et al.t19l synthesized the lactone intermediate of the 1-hydroxyethylene isostere with high yields and stereoselectivity. As summarized in Scheme 10 (Section 10.6.2), the titanium homoenolate is prepared from ethyl 3-iodopropionate. The iodide is metalated with zinc/copper couple to give the iodozinc homoenolate species. The alkyltitanium homoenolate is then generated by transmetalation of the iodozinc precursor with one of the several chlorotitanium isopropoxide species. The resulting titanium homoenolate reacts with a N-protected a-amino aldehyde, leading to a mixture of 45-diastereomers. In the last step, the product is lactonized. 

The diethyl 2-(ethoxycarbonyl)ethylphosphonate is prepared in 35% yield from sodium diethyl phosphite and ethyl 3-iodopropionate. -- Similarly, methyl 2,3-dibromopropionate reacts with sodium diethyl phosphite with fonnation of diethyl 2-(methoxycarbonyl)ethylphosphonate in low yield (15%). ° Most likely, these reactions occur via an elimination-addition process promoted by the sodium diethyl phosphite. Treatment of ethyl 3-bromobutyrate with sodium dibutyl phosphite in toluene at VO C affords dibutyl l-methyl-2-(ethoxycarbonyl)ethylphosphonate in 62% yield, ... 

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