Preparation of methylcyclopentane-1-d(1)

The title compound has been prepared in 70% yield by the reaction between 1 -chloro-1-methylcyclopentane and deuterotributylstannane, without solvent. Small amounts (0.7-3.5%) of unreacted starting material remained after the reaction and were removed by solvolytic HCl elimination with water or aqueo us sodium hydroxide, followed by oxidation with potassium permanganate or b romine addition at low temperature, which form products of low volatility. Small amounts of a by-product, deuterobutane, resulting from the cleavage o f the carbon-tin bond in the reactant were also observed in the product.