n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h;

n-butyllithium in tetrahydrofuran byproducts: Sn(n-Bu)4; disoln. of stannyl silyl ether in dry THF, cooling to -78°C (under Ar), dropwise addn. of n-BuLi in hexane (3 equiv.) (via syringe), stirring (-78°C, 15 min)quenching by rapid addn. of water at -78°C; warming to room temp., extn. with petroleum ether, flash chromy., eluation of tetraalkylstannane with hexane, eluation of product with ethyl acetate/hexane;

Yield given. Multistep reaction;

1: Li 2: (hydrolysis) View Scheme

1: diethyl ether 2: (i) BH3, THF, (ii) aq. H2O2, NaOH View Scheme

(hydrolysis);

(i) BH3, THF, (ii) aq. H2O2, NaOH; Multistep reaction;