2-chloro-ethynyladamant-2-ol

To a solution of 5.16ml 1.6M BuLi (8.26mMol) in 100ml ether was added dropwise a solution of 0.4g (4.12mmol) 1,2-dichlorethylene in 20ml ether at -78^oC under nitrogen. The solution was allowed to reach room temperature and then was stirred for 30 minutes to give a white suspension. O.5g adamantanone in 50ml ether and a trace of FeCl3 were added over 30 minutes before carefully heating to reflux for 30 minutes to turn immediately to a grey suspension. After cooling down to room temperature the reaction mixture was poured on ice-cold hydrochloric acid, extracted with ether and dried over potassium carbonate, to give 0.6g (85%) of a white-yellow compound, m.p. 115-117^oC. TLC (hexane/petrol/ethylacetate=1:1:1) yielded one single spot, RF=0.5; IR (nujol) 3605.8, 3317.9 (O-H), 2907.8, 2857.9, 2222.1 (C[[equivalence]]C), 796 (C-Cl) cm^-1; MS (m/z) 228 (M+NH4)⁺, 210 (M⁺), 193, 182, 174, 147, 105, 91. Crystals suitable for X-ray analysis were grown in chloroform/pentane using the slow evaporation method.