Preparation of methylcyclopentane-1-d1

Article abstract of DOI:10.1002/(SICI)1099-1344(20000315)43:3<237::AID-JLCR308>3.0.CO;2-F

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 aqueous sodium hydroxide, followed by oxidation with potassium permanganate or bromine addition at low temperature, which form products of low volatility. Small amounts of a by-product, deuterobutane, resulting from the cleavage of the carbon-tin bond in the reactant were also observed in the product.