Isopropyl iodide → HCID 22241954, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 10 mL (72 mmol) of diisopropylamine in 250 mL of tetrahydrofuran (THF) was added 28.6 mL (72 mmol) of BuLi (2.5 molar in cyclohexanes) at −20° C. After 20 minutes stirring, 9.2 g (83% pure) (28.3 mmol) of diethyl 2,3-diethylsuccinate was added at −40° C. and after addition the mixture was stirred for 2 h at room temperature. Then this mixture was cooled to −70° C. and a mixture of 4.3 mL (43 mmol) of 2-iodopropane and 7.4 mL (43 mmol) of hexamethylphosphoramide (HMPA) was added. After addition the cooling was removed and the mixture was stirred for four days. The volatiles were removed and 250 mL of ether was added. The organic layer was washed twice with 100 mL of water. The organic layer was isolated, dried over MgSO4, filtered and concentrated in vacuo yielding an orange oil. This oil was chromatographed over silica with CH2Cl2 yielding 2.3 g (30%) of a 96% pure product. According to gaschromatography (GC) only one isomer was present.

Provenance & Evidence