2,3-Dichloropropene → Ethyl 4-chloro-2,2-dimethylpent-4-enoate

Participants

Reaction Steps

Diisopropylamine (1.25 eq) was added to a reaction flask containing THF (tetrahydrofuran; 10.0-fold, V/W of ethyl isobutyrate) under N2. The mixture was cooled to less than −70° C., and n-butyllithium (2.7M; 1.14 eq) was added to the reaction mixture while the temperature was maintained at less than −65° C. The reaction mixture was slowly warmed to room temperature and then stirred for 2 hours under N2. The reaction mixture was then cooled to less than −70° C., and ethyl isobutyrate (1.0 eq) was added, followed by 2,3-dichloro-1-propene (1.09 eq), while the temperature was maintained at less than −70° C. The reaction was allowed to warm to room temperature and stirred overnight under N2. The reaction was then quenched with ice water (10.0-fold, V/W of starting material), and the pH adjusted to pH 7 with aqueous 6M HCl. The organic layer was separated, washed twice with brine, and dried over Na2SO4. The solvent was removed in vacuo and the product was taken on to the next step without further purification.

Provenance & Evidence