1: Cs2CO3; CuI; NaI 2: quinoline; D2 / Pd/BaSO4 / methanol / 16 h 3: 10 percent NaOH / ethanol 4: Skeletonema costatum / H2O / 0.02 h / sonicated View Scheme

1: CBr4; PPh3 2: Cs2CO3; CuI; NaI 3: quinoline; D2 / Pd/BaSO4 / methanol / 16 h 4: 10 percent NaOH / ethanol 5: Skeletonema costatum / H2O / 0.02 h / sonicated View Scheme

in ethylene glycol dimethyl ether T=-78°C; 0.25 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

in tetrahydrofuran; diethyl ether T=-78°C; 0.5 h; Yield given. Yields of byproduct given;