2-Trimethylsilyl-1,3-dithiane → 2-(4,4-Dimethylcyclohexylidene)-1,3-dithiane

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-trimethylsily-1,3-dithiane (42.3 g, 0.22 mol) in THF (400 mL) at 0° C. under an argon atmosphere was added a solution of n-butyl lithium (2.5 M in hexanes, 88 mL, 0.22 mol) and the mixture was cooled to −78° C. A solution of 4,4-dimethyl cyclohexanone (13.9 g, 0.11 mol) in THF (50 mL) was added over 10 min. After 2 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (200 mL). The aqueous phase was extracted with EtOAc (200 mL×2) and the combined organic layers were dried (MgSO4) and were evaporated. The reaction by-products were removed by vacuum distillation to yield the desired product as a white wax (21 g, 85%). MH+229

Provenance & Evidence