HCID 18783146, compound → HCID 18783147, compound

Participants

Reaction Steps

A solution of ethyl 3,3,5,5-tetramethylcyclohexylacetate 8 (1.8 g, 8.0 mmol) in ether (30 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (0.9 g, 24.0 mmol) in ether (30 ml), which was cooled in an ice bath. The reaction mixture was refluxed for 3 h, cooled and residual lithium aluminum hydnde was destroyed with water. The aqueous layer was separated and twice extracted with ether. The combined ether phases were washed with saline, dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography on silica gel, eluting with hexane--ethyl acetate mixture (4:1) to give 1.2 g (79%) of 11 as an oil. 1H NMR (CDCl3, TMS) δ: 0.89 and 1.00 (total 12H, both s, cyclohexane 3,5-CH3); 1.44 (2H, q, J=7 Hz, 2-CH2); 0.55-1.95 (8H, m, ring protons and OH) and 3.70 ppm (2H, t, J=7 Hz, CH2O).

Provenance & Evidence