4-Iodobutanoyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: tert-Butyl lithium (a 1.7 M solution in pentane; 0.33 ml, 0.56 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (188.1 mg, 0.56 mmol) in tetrahydrofuran (4 ml) at 0° under argon. After 15 minutes, a solution of 4-iodobutyryl chloride (129 mg, 0.56 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued overnight while the cooling bath attained room temperature. The mixture was quenched with water and extracted with ethyl ether. Evaporation of the dried (magnesium sulphate) extracts afforded an oil, which was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a colorless oil. was continued overnight while the cooling bath attained room temperature The mixture was quenched with water extracted with ethyl ether Evaporation of the dried (magnesium sulphate) extracts afforded an oil, which was purified by preparative TLC (20×20 cm, 1000μ silica plate; developed with 10% ethyl ether/hexane)