Diisopropylamine → Ethyl 2-benzyl-2-methyl-5-trimethylsilylpent-4-ynoate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.2 ml (1.58 gm) of diisopropylamine in 20 ml of dry tetrahydrofuran, was added dropwise a solution of n-butyllithium (9.7 ml, 1.6M) at 0° C. The solution was stirred at 0° C. for 30 min, then cooled to -78° C. A solution of 2.5 gm of ethyl 3-phenyl-2-methylpropionate in 10 ml of dry tetrahydrofuran was added. After 30 min., 3 gm of trimethylsilylpropargyl bromide in 10 ml dry tetrahydrofuran was added. The mixture was warmed up to 0° C. slowly and maintained at 0° C. for 1.75 hours. The reaction mixture was quenched with 5% hydrochloric acid and partitioned between ether and 5% hydrochloric acid. The ethereal layer, washed with brine solution and water was dried and evaporated in an oil. The oil was chromatographed on silica gel (5% ethyl acetate; petroleum ether). This procedure yielded the title compound, IR: 2170, 1738 cm-1.

Provenance & Evidence